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Journal articles on the topic 'Diospongin A'

Author: Grafiati

Published: 6 September 2023

Last updated: 7 September 2023

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1

Bates, Roderick W., and Ping Song. "Synthesis of diospongin A." Tetrahedron 63, no. 21 (May 2007): 4497–99. http://dx.doi.org/10.1016/j.tet.2007.03.058.

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2

Zúñiga, Andrea, Manuel Pérez, Zoila Gándara, Alioune Fall, Generosa Gómez, and Yagamare Fall. "Synthesis of diospongin A, ent-diospongin A and C-5 epimer of diospongin B from tri-O-acetyl-D-glucal." Arkivoc 2015, no. 7 (October 22, 2015): 195–215. http://dx.doi.org/10.3998/ark.5550190.p009.191.

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3

Bharath, Yada, Utkal Mani Choudhury, N. Sadhana, and Debendra K. Mohapatra. "The Mukaiyama type aldol reaction for the synthesis of trans-2,6-disubstituted tetrahydropyrans: synthesis of diospongin A and B." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9169–81. http://dx.doi.org/10.1039/c9ob01549c.

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The synthesis of 2,6-trans-disubstituted tetrahydropyrans following the Mukaiyama type aldol reaction through C–C bond formation demonstrates the practicality of this protocol in the total synthesis of diospongin A and B.

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4

Vaithegi, Kannan, and Kavirayani R. Prasad. "Total synthesis of (+)-diospongin A." Tetrahedron 76, no. 47 (November 2020): 131625. http://dx.doi.org/10.1016/j.tet.2020.131625.

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5

Chandrasekhar, S., T. Shyamsunder, S. Jaya Prakash, A. Prabhakar, and B. Jagadeesh. "First total synthesis of (−)-diospongin B." Tetrahedron Letters 47, no. 1 (January 2006): 47–49. http://dx.doi.org/10.1016/j.tetlet.2005.10.129.

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6

Meruva, Suresh Babu, Ramamohan Mekala, Akula Raghunadh, K. Raghavendra Rao, Vilas H. Dahanukar, T. V. Pratap, U. K. Syam Kumar, and P. K. Dubey. "Synthesis of tetrahedral diarylheptanoid ent-diospongin A and epimer-diospongin B by employing Julia–Kocienski olefination." Tetrahedron Letters 55, no. 34 (August 2014): 4739–41. http://dx.doi.org/10.1016/j.tetlet.2014.06.112.

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7

Cossy, Janine, Cyril Bressy, and Florent Allais. "A Short and Efficient Synthesis of (-)-Diospongin A." Synlett 2006, no. 20 (December 2006): 3455–56. http://dx.doi.org/10.1055/s-2006-956485.

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8

Hiebel, Marie-Aude, Béatrice Pelotier, and Olivier Piva. "Total synthesis of (+/−)-diospongin A via Prins reaction." Tetrahedron 63, no. 33 (August 2007): 7874–78. http://dx.doi.org/10.1016/j.tet.2007.05.089.

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9

Ho, Tse-Lok, Bin Tang, Guohua Ma, and Pengfei Xu. "Concise Synthesis of Yashabushidiol A and (±)-Diospongin A." Journal of the Chinese Chemical Society 59, no. 3 (March 2012): 455–58. http://dx.doi.org/10.1002/jccs.201100664.

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10

Meruva, Suresh Babu, Ramamohan Mekala, Akula Raghunadh, K. Raghavendra Rao, Vilas H. Dahanukar, T. V. Pratap, U. K. Syam Kumar, and P. K. Dubey. "ChemInform Abstract: Synthesis of Tetrahedral Diarylheptanoid ent-Diospongin A (I) and epimer-Diospongin B (II) by Employing Julia-Kocienski Olefination." ChemInform 46, no. 5 (January 15, 2015): no. http://dx.doi.org/10.1002/chin.201505215.

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11

Reddy, Chada Raji, Guvvala Balakrishna Reddy, and Boinapally Srikanth. "Stereoselective synthesis of a tetrahydropyranyl diarylheptanoid, ent-diospongin A." Tetrahedron: Asymmetry 22, no. 18-19 (October 2011): 1725–28. http://dx.doi.org/10.1016/j.tetasy.2011.10.006.

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12

Chandrasekhar, S., G. S. Kiran Babu, and Ch Raji Reddy. "Asymmetric synthesis of aza-diospongin A as an iNOS inducer." Tetrahedron: Asymmetry 20, no. 19 (October 2009): 2216–19. http://dx.doi.org/10.1016/j.tetasy.2009.09.013.

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13

Kumar, Rayala Naveen, and H. M. Meshram. "Total synthesis of (−)-diospongin A and (+)-cryptofolione via asymmetric aldol reaction." Tetrahedron Letters 52, no. 9 (March 2011): 1003–7. http://dx.doi.org/10.1016/j.tetlet.2010.12.070.

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14

More, Jesse. "Synthesis of (±)-Diospongin A: A Hetero-Diels-Alder and C-Glycosylation Approach." Synthesis 2010, no. 14 (May 10, 2010): 2419–23. http://dx.doi.org/10.1055/s-0029-1218784.

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15

More, Jesse D. "ChemInform Abstract: Synthesis of (.+-.)-Diospongin A: A Hetero-Diels-Alder and C-Glycosylation Approach." ChemInform 41, no. 48 (November 4, 2010): no. http://dx.doi.org/10.1002/chin.201048209.

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16

Yadav, J., B. Padmavani, B. V. Reddy, Ch Venugopal, and A. Rao. "Total Synthesis of Diospongin A via an Enzymatic Kinetic Resolution of (±)-Tetrahydropyranol Derived from Prins Cyclization." Synlett 2007, no. 13 (July 12, 2007): 2045–48. http://dx.doi.org/10.1055/s-2007-984886.

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17

Karlubíková, Ol'ga, Matej Babjak, and Tibor Gracza. "Tetrahydropyran synthesis by palladium(II)-catalysed hydroxycarbonylation of hexenols: synthesis of (±)-diospongin A and (+)-civet cat compound." Tetrahedron 67, no. 27-28 (July 2011): 4980–87. http://dx.doi.org/10.1016/j.tet.2011.04.045.

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18

Gharpure, Santosh J., Sumit P. Mane, Laxmi Narayan Nanda, and Manoj Kumar Shukla. "Stereoselective Synthesis of Donor-Acceptor Cyclopropapyranone by Intramolecular Cyclopropanation of Vinylogous Carbonates: Application to the Total Synthesis of (±)-Diospongin B." Israel Journal of Chemistry 56, no. 6-7 (January 6, 2016): 553–57. http://dx.doi.org/10.1002/ijch.201500088.

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19

Tong, Rongbiao, and Zhilong Li. "Asymmetric Total Syntheses of the trans-2-Aryl-6-alkyltetrahydropyrans Diospongin B and Parvistones D and E from a Common Precursor." Synthesis 48, no. 11 (April 12, 2016): 1630–36. http://dx.doi.org/10.1055/s-0035-1561592.

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20

Rybak, Taras, and Dennis G. Hall. "Stereoselective and Regiodivergent Allylic Suzuki–Miyaura Cross-Coupling of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of Absolute Stereochemistry of Diospongin B." Organic Letters 17, no. 17 (August 20, 2015): 4156–59. http://dx.doi.org/10.1021/acs.orglett.5b01906.

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21

Tadiparthi, Krishnaji, and Sourav Chatterjee. "Synthetic Approaches to Diospongins: A Two Decade Journey." SynOpen 06, no. 03 (July 2022): 141–57. http://dx.doi.org/10.1055/s-0040-1720032.

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AbstractTetrahydropyran units having multiple stereogenic centers serve as excellent building blocks for various active pharmaceutical ingredients (APIs). In particular, the presence of the unique molecular architecture of the trisubstituted tetrahydropyran (THP) unit in diospongins enhances their biological activity due to multiple stereogenic centers and has attracted attention from the synthetic community over the last two decades. In this review, we discuss synthetic approaches to chiral and racemic forms of diospongins during the period 2006–2020 in chronological order.

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22

Rybak, Taras, and Dennis G. Hall. "ChemInform Abstract: Stereoselective and Regiodivergent Allylic Suzuki-Miyaura Cross-Coupling of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of Absolute Stereochemistry of Diospongin B." ChemInform 47, no. 4 (January 2016): no. http://dx.doi.org/10.1002/chin.201604130.

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23

Clarke, Paul A., Nadiah Mad Nasir, Philip B. Sellars, Alejandra M. Peter, Connor A. Lawson, and James L. Burroughs. "Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland–Japp derived 2H-dihydropyran-4-ones: a total synthesis of diospongin B." Organic & Biomolecular Chemistry 14, no. 28 (2016): 6840–52. http://dx.doi.org/10.1039/c6ob01182a.

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24

Lee, Kiyoun, Hyoungsu Kim, and Jiyong Hong. "A Facile and Efficient Synthesis of 4-Hydroxy-2,6-cis-tetrahydropyrans via Tandem Cross-Metathesis/Thermal SN2′ Reaction: Protecting-Group-Free Synthesis of (±)-Diospongin A." Organic Letters 11, no. 22 (November 19, 2009): 5202–5. http://dx.doi.org/10.1021/ol902125d.

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25

Yao, Hongliang, Jingyun Ren, and Rongbiao Tong. "A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxidescycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A." Chem. Commun. 49, no. 2 (2013): 193–95. http://dx.doi.org/10.1039/c2cc37772a.

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26

Kumaraswamy, Gullapalli, and Dasa Rambabu. "A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps." Tetrahedron: Asymmetry 24, no. 4 (February 2013): 196–201. http://dx.doi.org/10.1016/j.tetasy.2013.01.005.

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27

Yao, Hongliang, Jingyun Ren, and Rongbiao Tong. "ChemInform Abstract: A Short and Flexible Route to Tetrahydropyran-4-ones via Conjugated Nitrile Oxides Cycloaddition and Oxa-Michael Cyclization: A Concise Diastereoselective Total Synthesis of (.+-.)-Diospongin A." ChemInform 44, no. 20 (April 25, 2013): no. http://dx.doi.org/10.1002/chin.201320153.

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28

Xian, Ming, Hua Wang, and Brian Shuhler. "Total Syntheses of Diospongins A and B." Synlett 2008, no. 17 (October 1, 2008): 2651–54. http://dx.doi.org/10.1055/s-0028-1083518.

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29

Stefan, Eric, Ansel P. Nalin, and Richard E. Taylor. "Concise enantioselective synthesis of diospongins A and B." Tetrahedron 69, no. 36 (September 2013): 7706–12. http://dx.doi.org/10.1016/j.tet.2013.05.081.

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30

Sabitha, Gowravaram, Pannala Padmaja, and Jhillu S Yadav. "A Concise Total Synthesis of Diospongins A and B." Helvetica Chimica Acta 91, no. 12 (December 2008): 2235–39. http://dx.doi.org/10.1002/hlca.200890242.

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31

Kawai, Nobuyuki, Sudhir Mahadeo Hande, and Jun'ichi Uenishi. "Stereoselective synthesis of (−)-diospongins A and B and their stereoisomers at C-5." Tetrahedron 63, no. 37 (September 2007): 9049–56. http://dx.doi.org/10.1016/j.tet.2007.06.081.

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32

Sawant, Kailas B., and Michael P. Jennings. "Efficient Total Syntheses and Structural Verification of Both Diospongins A and B via a Common δ-Lactone Intermediate." Journal of Organic Chemistry 71, no. 20 (September 2006): 7911–14. http://dx.doi.org/10.1021/jo061296f.

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33

Piva, Olivier, Ludovic Raffier, and Frédéric Izquierdo. "Desymmetrization of Hepta-1,6-dien-4-ol by Prins Reaction and Subsequent Cross-Metathesis: Access to Diospongine A Homologues." Synthesis 2011, no. 24 (November 4, 2011): 4037–44. http://dx.doi.org/10.1055/s-0031-1289588.

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34

Anada, Masahiro, Takuya Washio, Yudai Watanabe, Koji Takeda, and Shunichi Hashimoto. "A Short, Catalytic, Asymmetric Synthesis of Diospongins A and B by a One-Pot, Sequential Hetero-Diels-Alder/Mukaiyama-Michael Reaction Process." European Journal of Organic Chemistry 2010, no. 35 (October 27, 2010): 6850–54. http://dx.doi.org/10.1002/ejoc.201001125.

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35

Kumaraswamy, Gullapalli, Gajula Ramakrishna, Police Naresh, Bharatam Jagadeesh, and Balasubramanian Sridhar. "A Flexible Enantioselective Total Synthesis of Diospongins A and B and Their Enantiomers Using Catalytic Hetero-Diels−Alder/Rh-Catalyzed 1,4-Addition and Asymmetric Transfer Hydrogenation Reactions as Key Steps." Journal of Organic Chemistry 74, no. 21 (November 6, 2009): 8468–71. http://dx.doi.org/10.1021/jo901739y.

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36

Bates, Roderick W., and Ping Song. "Synthesis of Diospongin A." ChemInform 38, no. 35 (August 28, 2007). http://dx.doi.org/10.1002/chin.200735215.

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37

Chandrasekhar, S., T. Shyamsunder, S. Jaya Prakash, A. Prabhakar, and B. Jagadeesh. "First Total Synthesis of (-)-Diospongin B." ChemInform 37, no. 18 (May 2, 2006). http://dx.doi.org/10.1002/chin.200618220.

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38

Hiebel, Marie-Aude, Beatrice Pelotier, and Olivier Piva. "Total Synthesis of (+/-)-Diospongin A via Prins Reaction." ChemInform 38, no. 47 (November 20, 2007). http://dx.doi.org/10.1002/chin.200747205.

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39

Bressy, Cyril, Florent Allais, and Janine Cossy. "A Short and Efficient Synthesis of (-)-Diospongin A." ChemInform 38, no. 17 (April 24, 2007). http://dx.doi.org/10.1002/chin.200717197.

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40

Jun, Yin, Liu Zhihui, Han Na, and Xiao Bin. "Relative and Absolute Structures of Diospongin A, B and C." Planta Medica 75, no. 04 (March 2009). http://dx.doi.org/10.1055/s-2009-1216410.

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41

Chandrasekhar, S., G. S. Kiran Babu, and Ch Raji Reddy. "ChemInform Abstract: Asymmetric Synthesis of aza-Diospongin as an iNOS Inducer." ChemInform 41, no. 12 (March 23, 2010). http://dx.doi.org/10.1002/chin.201012194.

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42

Yadav, J. S., B. Padmavani, B. V. Subba Reddy, Ch Venugopal, and A. Bhaskar Rao. "ChemInform Abstract: Total Synthesis of Diospongin A via an Enzymatic Kinetic Resolution of (.+-.)-Tetrahydropyranol Derived from Prins Cyclization." ChemInform 39, no. 1 (January 1, 2008). http://dx.doi.org/10.1002/chin.200801218.

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43

Gharpure, Santosh J., Sumit P. Mane, Laxmi Narayan Nanda, and Manoj Kumar Shukla. "ChemInform Abstract: Stereoselective Synthesis of Donor-Acceptor Cyclopropapyranone by Intramolecular Cyclopropanation of Vinylogous Carbonates: Application to the Total Synthesis of (.+-.)-Diospongin B." ChemInform 47, no. 47 (November 2016). http://dx.doi.org/10.1002/chin.201647152.

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44

Li, Zhilong, and Rongbiao Tong. "ChemInform Abstract: Asymmetric Total Syntheses of the trans-2-Aryl-6-alkyltetrahydropyrans Diospongin B and Parvistones D and E from a Common Precursor." ChemInform 47, no. 43 (October 2016). http://dx.doi.org/10.1002/chin.201643180.

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45

Clarke, Paul A., Nadiah Mad Nasir, Philip B. Sellars, Alejandra M. Peter, Connor A. Lawson, and James L. Burroughs. "ChemInform Abstract: Synthesis of 2,6-trans- and 3,3,6-Trisubstituted Tetrahydropyran-4-ones from Maitland-Japp Derived 2H-Dihydropyran-4-ones: A Total Synthesis of Diospongin B." ChemInform 47, no. 49 (November 2016). http://dx.doi.org/10.1002/chin.201649147.

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46

Sabitha, Gowravaram, Pannala Padmaja, and Jhillu S. Yadav. "ChemInform Abstract: A Concise Total Synthesis of Diospongins A (VII) and B (VIII)." ChemInform 40, no. 18 (May 5, 2009). http://dx.doi.org/10.1002/chin.200918195.

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47

Kawai, Nobuyuki, Sudhir Mahadeo Hande, and Jun'ichi Uenishi. "ChemInform Abstract: Stereoselective Synthesis of (-)-Diospongins A and B and Their Stereoisomers at C-5." ChemInform 39, no. 4 (January 22, 2008). http://dx.doi.org/10.1002/chin.200804221.

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48

Sawant, Kailas B., and Michael P. Jennings. "Efficient Total Syntheses and Structural Verification of Both Diospongins A (IIa) and B (IIb) via a Common δ-Lactone Intermediate (I)." ChemInform 38, no. 6 (February 6, 2007). http://dx.doi.org/10.1002/chin.200706195.

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49

Kumaraswamy, Gullapalli, Gajula Ramakrishna, Police Naresh, Bharatam Jagadeesh, and Balasubramanian Sridhar. "ChemInform Abstract: A Flexible Enantioselective Total Synthesis of Diospongins A (I) and B (II) and Their Enantiomers Using Catalytic Hetero-Diels-Alder/Rh-Catalyzed 1,4-Addition and Asymmetric Transfer Hydrogenation Reactions as Key Steps." ChemInform 41, no. 12 (March 23, 2010). http://dx.doi.org/10.1002/chin.201012196.

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