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1
Phun, Lien Hoang. "Innovative approaches to carbocyclic and heterocyclic compounds using strained carbocycles". Diss., Georgia Institute of Technology, 2013. http://hdl.handle.net/1853/47542.
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Natural products and small molecules play a major role in drug development. However, using natural products as a source of medicine comes with many challenges, such as lack of natural abundance and difficulty in isolation. Consequently, synthetic organic chemistry is a solution in order to access these compounds in usable quantities. However, synthetic chemisty comes with its own challenges such as efficiency, chemoselectivity, stereoselectivity and enantioselectivity. Therefore, synthetic tools that addresses these challenges are required solve these limitations. This thesis discusses new methodologies using strained carbocycles (cyclopropanes and cyclopropenes) as the reactive subunit for the construction of different carbocyclic and heterocyclic compounds. The homo-Nazarov cyclization of alkenyl and heteroaryl cyclopropyl ketones was used in order to construct cyclohexenones, cyclohexenols, heteroaryl ring-fused cyclohexenones, dihydrofurans, furans and furanones in a mild and efficient manner. Benzofused heteroaromatic compounds were achieved via the Lewis acid-catalyzed cycloisomerization of cyclopropene-3,3-dicarbonyls and furan-3-carboxylates. These heteroaromatic compounds can be applied to medicinal chemistry and material science.
2
Das, Jayanta. "Trans formative reactions on carbocyclic compounds". Thesis, University of North Bengal, 2015. http://ir.nbu.ac.in/handle/123456789/1863.
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Ghosh, Pranab. "Studies on chemical reactions of carbocyclic compounds". Thesis, University of North Bengal, 1991. http://hdl.handle.net/123456789/767.
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Bright, Steven. "Acid induced cationic rearrangements of carbocyclic compounds". Thesis, University of Canterbury. Chemistry, 1988. http://hdl.handle.net/10092/7597.
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This thesis examines fluorosulfonic acid as a reagent for use in organic synthesis. The acid strength of fluorosulfonic acid gives access to rearrangement products not available with weaker acids.
The reaction of a selected series of benzyl carbinols with HSO₃F are reported. Reaction of 1-benzyl-2-methylcyclohexanol (1) gave cis-4a-methyl-1,2,3,4,4a,9a-hexahydrofluorene (2), while 1-benzyl -3-methylcyclohexanol (10) and 1-benzyl-4-methylcyclohexanol (11) were reduced to cis-1-benzyl-3-methylcyclohexane (12) and trans-1-benzyl-4-methylcyclohexane (13) respectively.
[Diagram in thesis]
6-Benzylspiro[4.5]decan-6-ol (4) underwent a ring expansion to give the propellane, tetracyclo[7.4.4.0¹⁹.0²⁷]heptadeca-2,4,6-triene (5). Reaction of 1-benzyl-trans-decalin-1-ol (6) with HSO₃F gave the natural product (±)-9a-carba-14α-morphinan (7), while spiro[3-exobenzylbicyclo[2,2,1]heptan-3-endo-ol-2,1'-cyclopentane] (41) gave pentacyclo [9.7.0.0¹,¹⁴.0³,⁸.0⁹,¹⁴]octadeca-3,5,7-triene (42).
The mechanism of rearrangement of 2-exo-benzylbicyclo[2.2.1] heptan-2-endo-ol (14) to 6-phenylbicyclo[3.2.1]oct-6-ene (16) was elucidated by the use of deuterium labeled substrates. Reaction of phenylethyl carbinols with HSO₃F afforded a route to bicyclic systems, for example 1-(2-phenylethyl)cyclohexanol (59) gave cis-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (61) and spiro[cyclohexane-1,1-indane] (60), while 2-methyl-1-(2- phenylethyl)cyclohexanol (64) gave a mixture of cis- (65) and trans-4a-methyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (66).
[Diagram in thesis]
Reaction of 1-(2-phenylethyl)-2,2,6-trimethylcyclohexanol (70) gave predominantly 1β,4aβ, 10 aβ-trimethyl-1,2,3,4,4a,9,10,10a octahydrophenanthrene (72) with a small amount of the 1a,4aβ,10aβ-trimethyl-isomer (73) while reaction of 2-exo-(2- phenylethyl)bicyclo[2,2,1 ]heptan-2-endo-ol (74) gave tetracyclo[10.2.1.0¹,¹⁰.0⁴,⁹]pentadeca-4,6,8-triene (75).
Phenylpropyl carbinols provide an entry to spiro products. Reaction of 1-(3-phenylpropyl)cyclohexanol (85) gave spiro[cyclohexane-1,1-tetralin] (86), while 2-methyl-1-(3- phenylpropyl)cyclohexanol (87) gave trans-2'-methylspiro[ cyclohexane-1,1-tetralin] (88).
[Diagram in thesis]
1,4-Diphenylbutan-1-ol (95) afforded 1-phenyl-1,2,3,4- tetrahydronapthalene (96) and 2,5-diphenylpentan-2-ol (97) gave an analogous product (98). 1,4-Di-(1-hydroxy-4-phenylbutan-1-yl)benzene (99) gave the two diastereoisomers of 1,4-di-(1,2,3,4-tetrahydronapth-1-yl)benzene (100), which on oxidation gave 1,4-di-(1-naphthyl) benzene (101).
Fluorosulfonic acid has been shown to be a synthetic reagent for the generation of several novel spiro, reduction, cyclisation and rearrangement products not accessible under weaker acid conditions.
5
Van, Eeden Nestor. "Synthesis of some potential antimicrobial carbocyclic compounds". Thesis, Cape Technikon, 1994. http://hdl.handle.net/20.500.11838/745.
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Thesis (M. Diploma in Technology (Chemistry))--Cape Technikon, 1994Some naturally occurring compounds containing the naphtho [2,3 - c] pyran ring system have been found to be useful antibiotic agents and thus the laboratory synthesis ofthese compounds and their derivatives are of importance in the medical field. Their antibiotic and even antineoplastic activities are attributed to their potential to act as alkylating agents, via a bioreductive process. This thesis deals with studies directed towards the synthesis of some benzo [c] pyrans as these compounds also possess the correct structural configuration to undergo the bioreductive process, and act as alkylating agents to cellular nucleic acids. Chapter Two describes the synthesis 00,4 dihydro - 1,3 - dimethyl- IH - benzo - [cl pyran - 5,8 - quinone (13) by employing a base induced cyclization with potassium tertiary butoxide. This compound was proven to be biologically active against both Gram positive and Gram negative organisms. (±) (1R, 3R, 4R) - 3,4 - Dihydro - 4 - hyroxy -1,3 - dimethyl- 1H - benzo [e] pyran - 5,8quinone (17) and its 4 S diastereomer (18) were synthesized with cerium (IV) ammonium nitrate as the cyclizing reagent. Antimicrobial evaluation ofcompound (17) displayed inhibitory activity against both Gram positive and Gram negative organism growth. This is discussed in Chapter Three. In Chapter Four, the synthesis ofthe benzo analogue ofthe naturally occurring naphthopyran antibiotic, hongconin, is discussed. The synthetic route used for this synthesis could well be applied to synthesise hongconin.
6
Pradhan, Nagendra Narayan. "Studies on the chemical reactions of carbocyclic compounds". Thesis, University of North Bengal, 2002. http://hdl.handle.net/123456789/743.
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Mothay, jyotsna. "Studies on the transformative reactions of carbocyclic compounds". Thesis, University of North Bengal, 2002. http://hdl.handle.net/123456789/771.
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Singha, Rabindranath. "Chemical transformation of carbocyclic compounds and development of novel reaction protocols". Thesis, University of North Bengal, 2021. http://ir.nbu.ac.in/handle/123456789/4326.
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Dutta, Gopal. "Chemical investigation of naturally occurring carbocyclic ring compounds". Thesis, University of North Bengal, 1989. http://hdl.handle.net/123456789/836.
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Lau, Clifford James. "A study of several interesting carbocyclic molecules /". The Ohio State University, 1987. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487584612166485.
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Chakraborty, Satyajit. "Studies on oxidative and reductive reactions of carbocyclic compounds". Thesis, University of North Bengal, 1988. http://hdl.handle.net/123456789/709.
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12
Witherington, Jason. "Novel synthetic methods enabling the construction of biologically active compounds". Thesis, University of Reading, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.386942.
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Chakraborty, Prasanta. "Chemical transformation of carbocyclic compounds and screening for their biological activity". Thesis, University of North Bengal, 2011. http://hdl.handle.net/123456789/1387.
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Worakun, Tanachat. "Palladium and rhodium catalysed construction of carbocyclic and heterocyclic compounds". Thesis, Queen's University Belfast, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.317069.
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Niger, Robert J. "Application of organosilanes in [3 + 2] annulation approaches to carbocyclic compounds". Thesis, Massachusetts Institute of Technology, 1999. http://hdl.handle.net/1721.1/85342.
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Singha, Rabindranath. "Chemical transformation of carbocyclic compounds and development of novel reaction protocols". Thesis, University of North Bengal, 2021. http://ir.nbu.ac.in/handle/123456789/4348.
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17
Atim, Silvia. "Studies of spin alignment in ferrocenylsilane compounds and in regiospecific oxidation reactions of 1,9-dimethylpentacyclo [5.4.0.02,6.03,10.05,9]undecane-8,11-dione". Thesis, University of North Texas, 2006. https://digital.library.unt.edu/ark:/67531/metadc5330/.
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Part I. The syntheses of a series of stable ferrocenylsilane compounds and their corresponding polyradical cations are reported. Electron spin properties of these molecules were investigated by cyclic voltammetry, ESR, and magnetic susceptibility measurements. All the compounds presented, showed significant electronic communication (>100 mV) between the redox centers by CV.
Part II. Baeyer-Villiger oxidation of (1,9-dimethyl-PCU-8,11-dione) was performed using m-chloroperoxybenzoic acid in 1:2 molar ratios. The product obtained was the corresponding dilactone 113. The structure of the reaction products was established unequivocally via single crystal X-ray diffraction methods. The reaction of the 1,9-dimethyl-PCU-8,11-dione with 1:1 molar ratio of m-chloroperoxybenzoic acid produced again the dilactone 113, and not the expected monolactone 114. Ceric ammonium nitrate (CAN) promoted oxidation reaction of 1,9-dimethyl-PCU-8,11-dione afforded a mixture of dimethylated lactones, which indicated unique reaction mechanism pathways. These individual isomers, 115 and 116, have been isolated from these mixtures via column chromatography by using silica gel as adsorbent followed by fractional recrystallization of individual chromatography fractions. Structures of these pure products have been established unequivocally by application of single crystal X-ray crystallographic methods.
18
Song, Eunho Krafft Marie E. "Ring-closing metathesis for the synthesis of carbocyclic and heterocyclic intramolecular Baylis-Hillman adducts". Diss., 2005. http://etd.lib.fsu.edu/theses/available/etd-05062005-172529.
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Thesis (M.S.)--Florida State University, 2005.Advisor: Dr. Marie E. Krafft, Florida State University, College of Arts and Sciences, Dept. of Chemistry and Biochemistry. Title and description from dissertation home page (viewed Sept. 19, 2005). Document formatted into pages; contains 147 pages. Includes bibliographical references.
19
Ghosh, Amrita. "Cycloaddition-Based Approaches to Bio-active Natural Products". Thesis, 2019. http://hdl.handle.net/10821/8197.
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Natural products regime has been recognized as an invaluable source of compounds of
medicinal importance. While some natural products are directly used as drugs, some drugs are
derived from natural products by modification of structures. In some cases the pharmacophore is
placed in a new backbone that replaces the core skeleton present in the natural product. Thus
synthesis of natural products continues to be in the fore front of organic chemistry research.
Carbocyclic compounds having ring sizes four to six are found in a large number of natural
products with promising biological activities. Cycloaddition reactions such as [2 + 2] and [4 + 4] can
be employed to access directly compounds with four and six membered rings. Ring expansion of four
membered rings is one of the commonly employed approaches to construct five membered rings.
This proposed investigation will employ a combination of the above approaches for synthesis of
bioactive natural products containing four to six memebered rings.
Synthesis of optically active natural products using naturally occurring optically active materials is
the most efficient way when their availability and adaptability are fulfilled. However, such cases are
rare as great variety of natural products exist while adaptable chiral compounds are very limited.
Therefore, finding certain common chiral pools adaptable to versatile target molecules is one of the
most important tasks in organic synthesis. A programme has been initiated in July, 2010 under the
supervision of Professor Subrata Ghosh, F.A.Sc, F.N.A Department of Organic Chemistry, Indian
Association for the Cultivation of Science, Jadavpur, Kolkata – 700 032 for the synthesis of
enantiopure organic compounds starting from nature’s chiral pool starting material D-mannitol.
Investigation embodied in this dissertation entitled “Cycloaddition-Based Approaches to
Bio-active Natural Products” is directed towards the development of synthetic methodologies for
some fused carbocyclic system present in natural products.
The present thesis addresses the above mentioned themes of contemporary interest in organic
chemistry and is presented in three chapters. In Chapter 1, a brief review on construction of
cyclobutane ring system is described. Chapter 2 deals with synthetic studies toward kelsoene.
Approach to the asymmetric synthesis of a functionalized tricyclo[6.2.0.0
2,6
]decane ring system
present in kelsoene and poduran employing stereocontrolled copper (I)-catalyzed intramolecular
[2+2] photocycloaddition, and RCM reaction as the key steps. Chapter 3 deals with synthetic studies
on erythrodiene and spirojatamol. The key steps involve (i) pinacol-type rearrangement of a
cyclobutane derivative, (ii) copper(I)-catalyzed intramolecular [2 + 2] photocaycloaddition of a diene
prepared from (+) dihydrocarvone to form oxabicyclo[3.2.0]heptanes derivative.
ii
The subject matter of each part has been structured under following headings: Introduction,
Background, Results and Discussion, Conclusion, References, Experimental and NMR Spectra.
In keeping with the general practice of reporting scientific observations, due
acknowledgements have been made to the findings of other investigators.A Thesis Submitted for the Degree of Doctor of Philosophy (Science) of Jadavpur University by AMRITA GHOSH
Research had been conducted in the division of Organic chemistry under IACS fellowship under the supervision of Prof. Subrata Ghosh, OC
20
Smith, Christopher Dennis. "Development of formal inverse electron demand Diels-Alder and electrocyclic reactions for the construction of carbocyclic and heterocyclic compounds". 2009. http://link.library.utoronto.ca/eir/EIRdetail.cfm?Resources__ID=968433&T=F.
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Singh, Jatinder. "C-H activation and multi-functionalization of carbocyclic rings bound to the sandwich compound, (n5-RCp)Co(n4-C4Ph3R')". Thesis, 2017. http://localhost:8080/iit/handle/2074/7258.
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22
"Synthetic studies of carbocycles from carbohydrates". Thesis, 2008. http://library.cuhk.edu.hk/record=b6074641.
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An enone was synthesized from delta-D-gluconolactone in four steps, involving a one-pot TPAP oxidation-K2CO3-mediated intramolecular Horner-Wadsworth-Emmons (HWE) olefination as the key step.In this thesis, a review regarding intramolecular direct aldol reaction from 1971 to 2008 is presented. The background information on pseudo-acarviosin, valiolamine and its containing compounds, gabosines and human glutathione transferase (hGST) is introduced.
Intramolecular direct aldol reaction was investigated for the construction of cyclohexanones and cycloheptanones from carbohydrates. Amine bases, amide bases and L-proline were employed to facilitate cyclization of 1,5- and 1,6-diketones successfully. These 1,5- and 1,6-diketones were prepared from carbohydrates by standard transformations. Different bases were employed to promote cyclization of 1,5-diketone derived from D-glucose to give cyclohexanones stereoselectively.
Intramolecular nitrile oxide-alkene cycloaddition (INOC) was studied with sugar derivatives having free hydroxyl groups. The INOC reaction, by incorporating chloramine-T and silica gel for the formation of nitrile oxide from oxime, proceeded smoothly with one, two, and four unmasked hydroxyl groups to give cyclopentanes and cyclohexanes.
The polyhydroxylated carbocycles constructed from sugars were successfully transformed into a variety of target molecules including pseudo-acarviosin, valiolamine and its containing compounds and gabosines. A series of 2-crotonyloxymethyl-(4 R,5R,6R)-4,5,6-trihydroxy-2-cyclohexenone (COTC) analogues as inhibitors of hGST were prepared in order to study the structure-activity relationships.
Cheng, Hau Man.
Adviser: Tony K. M. Shing.
Source: Dissertation Abstracts International, Volume: 70-06, Section: B, page: 3508.
Thesis (Ph.D.)--Chinese University of Hong Kong, 2008.
Includes bibliographical references (leaves 214-224).
Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Abstracts in English and Chinese.
School code: 1307.
23
Grové, Jacobus Johannes Cronjé. "Samarium(II) iodide mediated conversion of carbohydrates into carbocycles". Thesis, 2012. http://hdl.handle.net/10210/7455.
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D.Phil.The topic of this thesis centres around the construction of carbocycles from carbohydrates involving the use of SmI2 as reagent. Carbocycles, in particular functionalised cyclopentanes, form important substructures in a plethora of natural compounds, many of which are biologically active. The conversion of carbohydrates into stereodefined cyclopentanoids represents an attractive means of generating this type of compounds. The SmI2-mediated cyclisation of hex-5-enals, derived from suitably substituted carbohydrate precursors via a zinc-mediated Grob-fragmentation reaction, was found to be a facile reaction generating stereodefined cyclopentanols in moderate yields. The effect of varying stereochemistry and substitution pattern on the outcome of the cyclisation was also investigated. In order to achieve a more efficient route to the cyclic products, a Grobfragmentation based on SmI2 was investigated. The substituent at the anomeric position of the carbohydrate was found to be crucial to the success of the fragmentation. This protocol gave rise to conditions under which fragmentation and cyclisation could be effected in a tandem fashion mediated by SmI2. Various attempts at intermolecular trapping of the organosamarium species generated after cyclisation proved fruitless. In order to circumvent these obstacles a tandem radical bicyclisation reaction was investigated for the construction of highly functionalised bicyclic ring systems. This approach proved to be a successful alternative for incorporating functionality at the exocyclic carbon atom which is otherwise difficult to achieve. The second part of this work is directed at the synthesis of stereodefined alkoxyaminocyclopentanes from carbohydrates promoted by SmI2. The intramolecular trapping of a radical by an oxime ether represents an attractive means of generating these compounds. The preparation of the iodo oxime ether starting materials from suitably substituted carbohydrates is discussed. The radical cyclisation under the action of SmI2 was found to be a facile process providing a rapid route to aminocyclopentanes which are used as key intermediates for the preparation of carbocyclic glycosidase inhibitors and analogues. In the third part of this work, the construction of functionalised cyclobutanols from carbohydrate precursors is discussed. The 4-exo-trig cyclisation holds promise as a general route for the stereoselective synthesis of highly functionalised cyclobutanols. Initial attempts at the 4-exo-trig cyclisation proved fruitless. It was subsequently established that the radical acceptor plays a crucial role in the success of the transformation. This led to the isolation of the first carbohydrate derived cyclobutanol. The final part of this thesis involves the development of a new approach for the conversion of suitably functionalised pentose derivatives into chiral cyclopentanols. Cyclisation of a ribose derived hemiacetal via its in situ formed hex-5-ynal is discussed. This approach opens new possibilities for the construction of complex carbocycles from readily available carbohydrate starting materials.
24
"Construction of carbocycles from carbohydrates via 1,3-dipolar cycloadditions". 2007. http://library.cuhk.edu.hk/record=b5893442.
Pełny tekst źródłaStreszczenie:
Kwok, Wun Sang.Thesis (M.Phil.)--Chinese University of Hong Kong, 2007.
Includes bibliographical references (leaves 147-152).
Abstracts in English and Chinese.
Acknowledgment --- p.i
Table of Contents --- p.ii
Abstract --- p.iii
Abstract (Chinese Version) --- p.iv
Abbreviation --- p.v
Chapter 1. --- Introduction --- p.1
Chapter 1.1 --- General Background --- p.1
Chapter 1.1.1 --- "1,3-Dipolar Cycloaddition" --- p.1
Chapter 1.1.2 --- Structure of Preparation of Nitrile Oxide --- p.3
Chapter 1.2 --- Intramolecular Nitrile Oxide Alkene Cyclization (INOC) --- p.7
Chapter 1.2.1 --- INOC in Organic Synthesis --- p.7
Chapter 1.2.2 --- Formation of Oximolactone as Unwanted Reaction in INOC --- p.10
Chapter 1.2.3 --- Nitrile Oxide Alkene Cyclization with Free Hydroxyl Group --- p.11
Chapter 1.3 --- Natural Occurring Gabosine --- p.14
Chapter 1.3.1 --- "Structure, Biological Effect and Syntheses of Gabosines" --- p.14
Chapter 1.3.2 --- Synthesis of Gabosine O and its 4-epimer --- p.17
Chapter 1.4 --- Protected 6-dehydroxy-Pseudo-a-D-Talose --- p.21
Chapter 1.4.1 --- Structures and Biological Effects of Valienamine and its Derivatives --- p.21
Chapter 1.4.2 --- Structural and Biological Studies of Valienamine by Our Group --- p.23
Chapter 2. --- Results and Discussion --- p.28
Chapter 2.1 --- Studies on INOC of Sugar Derivatives with Free Hydroxyl Group(s) --- p.28
Chapter 2.2 --- Enantiospecific Synthesis of 4-epi-Gabosine O --- p.47
Chapter 2.3 --- Enantiospecific Synthesis of Gabosine O --- p.84
Chapter 2.4 --- Synthesis of 6-Deoxy-Pseudo-a-D-Talose --- p.87
Chapter 3. --- Conclusion --- p.95
Chapter 4. --- Experimental --- p.100
References --- p.147
Appendix NMR spectra --- p.153
25
"Construction of carbocycles from carbohydrates via 1,3-dipolar cycloaddition". Thesis, 2011. http://library.cuhk.edu.hk/record=b6075206.
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A 5-membered INOC cycloadduct 84 was employed to prepare alcohol 91, which was transformed into several cyclopent-2-enone derivatives 94-96.By using intramolecular nitrile oxide-alkene cycloaddition (INOC) as the kep step to construct hydroxylated carbocycles, gabosine F was synthesized for the first time from L-arabinose. Hence, theoretically, gabosine B, which is the enantiomer of gabosine F, can also be synthesized from D-arabinose by the same synthetic strategy.
In this thesis, the background information on the construction of carbocycles from carbohydrates via intramolecular 1,3-dipolar cycloaddition is presented. A review regarding the syntheses of gabosine B and cocaine are also descibed.
Starting with D-ribose, INAC of nitrones 113, 129, and 140, bearing an alpha/beta-unsaturated ester as the dipolarophile was studied. The INAC endo-cycloadduct 141 (cycloheptane) was converted into natural cocaine sucessfully, together with cocaine analogues 162,169,170,173,175, and 177.
The regioselectivity of intramolecular nitrone-alkene cycloaddition (INAC) was studied. The INAC of hept-6-enose nitrone 98, with a 3,4- trans-pentylidene acetal as the only blocking group, afforded endo-cycloadduct 97 (cycloheptane) exclusively. This result concluded that the regiospecific outcome of this INAC reaction is due to the present of the 3,4-trans-pentylidene acetal blocking group.
To investigate the regioselectivity in INAC of hex-5-enose with a 2,3- trans-pentylidene acetal blocking group, nitrones 178 and 195 were prepared from D-mannitol. endo-Cycloadducts (cyclohexanes) were afforded exclusively.
So, King Ho.
Adviser: Kung Ming Tony Shing.
Source: Dissertation Abstracts International, Volume: 73-06, Section: B, page: .
Thesis (Ph.D.)--Chinese University of Hong Kong, 2011.
Includes bibliographical references (leaves 165-171).
Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [201-] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Abstract also in Chinese.
26
Sunasee, Rajesh. "Methodology and natural product synthesis carbocycles, culpin and sorbicillactone A /". Phd thesis, 2009. http://hdl.handle.net/10048/680.
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Thesis (Ph. D.)--University of Alberta, 2009.Title from pdf file main screen (viewed on Dec. 21, 2009). "A thesis submitted to the Faculty of Graduate Studies and Research in partial fulfillment of the requirements for the degree of Doctor of Philosophy, Chemistry Department, University of Alberta." Includes bibliographical references.