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    Sch 47918: a novel PAF antagonist from the fungus Phoma sp
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1992, 57, 22, 5817–5818
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    https://doi.org/10.1021/jo00048a008
    Published October 1, 1992
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    Cited By

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    This article is cited by 39 publications.

    1. Jinhua Hu, Zhenxing Zou, Yuchan Chen, Saini Li, Xiaoxia Gao, Zhaoming Liu, Yanlin Wang, Hongxin Liu, Weimin Zhang. Neocucurbols A–H, Phomactin Diterpene Derivatives from the Marine-Derived Fungus Neocucurbitaria unguis-hominis FS685. Journal of Natural Products 2022, 85 (8) , 1967-1975. https://doi.org/10.1021/acs.jnatprod.2c00249
    2. Paul R. Leger, Yusuke Kuroda, Stanley Chang, Justin Jurczyk, Richmond Sarpong. C–C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins. Journal of the American Chemical Society 2020, 142 (36) , 15536-15547. https://doi.org/10.1021/jacs.0c07316
    3. Junrong Huang, Wenli Bao, Shuangping Huang, Wei Yang, Zhu Lizhi, Guangyan Du, Chi-Sing Lee. Formal Synthesis of (+)-Phomactin A. Organic Letters 2018, 20 (23) , 7466-7469. https://doi.org/10.1021/acs.orglett.8b03242
    4. Guangyan Du, Wenli Bao, Junrong Huang, Shuangping Huang, Hong Yue, Wei Yang, Lizhi Zhu, Zhenhao Liang, and Chi-Sing Lee . Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy. Organic Letters 2015, 17 (9) , 2062-2065. https://doi.org/10.1021/acs.orglett.5b00586
    5. Jennifer Ciesielski, Kevin Cariou, and Alison J. Frontier . A Macrocyclic β-Iodoallenolate Intermediate Is Key: Synthesis of the ABD Core of Phomactin A. Organic Letters 2012, 14 (16) , 4082-4085. https://doi.org/10.1021/ol3017116
    6. Grant S. Buchanan, Kevin P. Cole, Yu Tang, and Richard P. Hsung . Total Synthesis of (±)-Phomactin A. Lessons Learned from Respecting a Challenging Structural Topology. The Journal of Organic Chemistry 2011, 76 (17) , 7027-7039. https://doi.org/10.1021/jo200936r
    7. Jie Huang,, Huan Wang,, Chunrui Wu, and, William D. Wulff. Intramolecular Cyclohexadienone Annulations of Fischer Carbene Complexes:  Model Studies for the Synthesis of Phomactins. Organic Letters 2007, 9 (15) , 2799-2802. https://doi.org/10.1021/ol070904q
    8. William P. D. Goldring and, Gerald Pattenden. The Phomactins. A Novel Group of Terpenoid Platelet Activating Factor Antagonists Related Biogenetically to the Taxanes. Accounts of Chemical Research 2006, 39 (5) , 354-361. https://doi.org/10.1021/ar050186c
    9. Punit P. Seth and, Nancy I. Totah. Studies toward the Tricyclic Core of Phomactin A. Synthesis of the Reduced Furanochroman Subunit. Organic Letters 2000, 2 (16) , 2507-2509. https://doi.org/10.1021/ol0061788
    10. Li Zhang, Bo Zhang, Ao Zhu, Shuang He Liu, Rui Wu, Xuan Zhang, Zhengren Xu, Ren Xiang Tan, Hui Ming Ge. Biosynthesis of Phomactin Platelet Activating Factor Antagonist Requires a Two‐Enzyme Cascade. Angewandte Chemie International Edition 2023, 62 (47) https://doi.org/10.1002/anie.202312996
    11. Li Zhang, Bo Zhang, Ao Zhu, Shuang He Liu, Rui Wu, Xuan Zhang, Zhengren Xu, Ren Xiang Tan, Hui Ming Ge. Biosynthesis of Phomactin Platelet Activating Factor Antagonist Requires a Two‐Enzyme Cascade. Angewandte Chemie 2023, 135 (47) https://doi.org/10.1002/ange.202312996
    12. Lantian Sun, Junrong Huang, Bo Wang, Guangyan Du, Chi‐Sing Lee. Formal Synthesis of (+)‐Phomactin A via a Prins/Conia‐ene Cascade and γ‐Hydroxylation Strategy. ChemistrySelect 2023, 8 (42) https://doi.org/10.1002/slct.202304204
    13. Mahendra Rai, Aniket Gade, Beata Zimowska, Avinash P. Ingle, Pramod Ingle. Marine-derived Phoma—the gold mine of bioactive compounds. Applied Microbiology and Biotechnology 2018, 102 (21) , 9053-9066. https://doi.org/10.1007/s00253-018-9329-2
    14. Masahiro Ishino, Hitoshi Kamauchi, Kazuhiko Takatori, Kaoru Kinoshita, Takashi Sugita, Kiyotaka Koyama. Three novel phomactin-type diterpenes from a marine-derived fungus. Tetrahedron Letters 2016, 57 (39) , 4341-4344. https://doi.org/10.1016/j.tetlet.2016.08.016
    15. Marcel Jaspars, Rainer Ebel, Hai Deng. Diversity of organic structures of marine microbial origin with drug potential. 2015, 361-380. https://doi.org/10.1002/9781118500354.ch16
    16. Jeffrey Y. W. Mak, Rebecca H. Pouwer, Craig M. Williams. Naturstoffe mit Anti‐Bredt‐ und Brückenkopf‐Doppelbindung. Angewandte Chemie 2014, 126 (50) , 13882-13906. https://doi.org/10.1002/ange.201400932
    17. Jeffrey Y. W. Mak, Rebecca H. Pouwer, Craig M. Williams. Natural Products with Anti‐Bredt and Bridgehead Double Bonds. Angewandte Chemie International Edition 2014, 53 (50) , 13664-13688. https://doi.org/10.1002/anie.201400932
    18. Jennifer Ciesielski, Alison Frontier. The Phomactin Natural Products from Isolation to Total Synthesis: A Review. Organic Preparations and Procedures International 2014, 46 (3) , 214-251. https://doi.org/10.1080/00304948.2014.903142
    19. Masahiro Ishino, Kaoru Kinoshita, Kunio Takahashi, Takashi Sugita, Motoo Shiro, Kimiko Hasegawa, Kiyotaka Koyama. Phomactins K–M, three novel phomactin-type diterpenes from a marine-derived fungus. Tetrahedron 2012, 68 (41) , 8572-8576. https://doi.org/10.1016/j.tet.2012.08.013
    20. Yu Tang, Kevin P. Cole, Richard P. Hsung. Phomactin A. 2012, 183-210. https://doi.org/10.1007/978-3-642-34065-9_8
    21. Grant S. Buchanan, Kevin P. Cole, Gang Li, Yu Tang, Ling-Feng You, Richard P. Hsung. Constructing the architecturally distinctive ABD-tricycle of phomactin A through an intramolecular oxa-[3+3] annulation strategy. Tetrahedron 2011, 67 (52) , 10105-10118. https://doi.org/10.1016/j.tet.2011.09.111
    22. Rainer Ebel. Terpenes from Marine-Derived Fungi. Marine Drugs 2010, 8 (8) , 2340-2368. https://doi.org/10.3390/md8082340
    23. Masahiro Ishino, Nobuto Kiyomichi, Kazuhiko Takatori, Takashi Sugita, Motoo Shiro, Kaoru Kinoshita, Kunio Takahashi, Kiyotaka Koyama. Phomactin I, 13-epi-Phomactin I, and Phomactin J, three novel diterpenes from a marine-derived fungus. Tetrahedron 2010, 66 (14) , 2594-2597. https://doi.org/10.1016/j.tet.2010.02.040
    24. Timothy J. Blackburn, Madeleine Helliwell, Michael J. Kilner, Alan T.L. Lee, Eric J. Thomas. Further studies of an approach to a total synthesis of phomactins. Tetrahedron Letters 2009, 50 (26) , 3550-3554. https://doi.org/10.1016/j.tetlet.2009.03.042
    25. Peter D.P. Shapland, Eric J. Thomas. Synthesis of precursors of phomactins using [2,3]-Wittig rearrangements. Tetrahedron 2009, 65 (21) , 4201-4211. https://doi.org/10.1016/j.tet.2009.03.031
    26. Graham McGowan, Eric J. Thomas. Synthesis of macrocyclic precursors of phomactins using [2,3]-Wittig rearrangements. Organic & Biomolecular Chemistry 2009, 7 (12) , 2576. https://doi.org/10.1039/b903256h
    27. Dawei Teng, Bo Wang, Alex J. Augatis, Nancy I. Totah. Studies toward the synthesis of phomactin A. An approach to the macrocyclic core. Tetrahedron Letters 2007, 48 (26) , 4605-4607. https://doi.org/10.1016/j.tetlet.2007.04.122
    28. William P.D. Goldring, Stephen P.H. Alexander, David A. Kendall, Gerald Pattenden. Novel phomactin analogues as PAF receptor ligands. Bioorganic & Medicinal Chemistry Letters 2005, 15 (13) , 3263-3266. https://doi.org/10.1016/j.bmcl.2005.04.048
    29. Andrew S Balnaves, Graham McGowan, Peter D.P Shapland, Eric J Thomas. Approaches to the total synthesis of phomactins. Tetrahedron Letters 2003, 44 (13) , 2713-2716. https://doi.org/10.1016/S0040-4039(03)00341-1
    30. Christopher M. Diaper, William P. D. Goldring, Gerald Pattenden. A total synthesis of (±)-phomactin A. Org. Biomol. Chem. 2003, 1 (22) , 3949-3956. https://doi.org/10.1039/B307986D
    31. Hiroaki Miyaoka, Yasuji Yamada. Total Synthesis of Bioactive Marine Terpenoids. Bulletin of the Chemical Society of Japan 2002, 75 (2) , 203-222. https://doi.org/10.1246/bcsj.75.203
    32. Jean-François Verbist, Claire Sallenave, Yves-François Pouchus. Marine Fungal Substances. 2000, 979-1092. https://doi.org/10.1016/S1572-5995(00)80059-9
    33. Jun’ichi Kobayashi, Masami Ishibashi. Marine Natural Products and Marine Chemical Ecology. 1999, 415-649. https://doi.org/10.1016/B978-0-08-091283-7.00055-2
    34. Hiroaki Miyaoka, Yasuhiro Saka, Shotaro Miura, Yasuji Yamada. Total synthesis of phomactin D. Tetrahedron Letters 1996, 37 (39) , 7107-7110. https://doi.org/10.1016/0040-4039(96)01585-7
    35. Aiya Sato. The Search for New Drugs from Marine Organisms. Journal of Toxicology: Toxin Reviews 1996, 15 (2) , 171-198. https://doi.org/10.3109/15569549609064083
    36. Andrew Ayscough, Mark Whittaker. Patent Update: Pulmonary-Allergy, Dermatological, Gastrointestinal & Arthritis: Platelet-activating factor receptor antagonists. Expert Opinion on Therapeutic Patents 1995, 5 (7) , 653-672. https://doi.org/10.1517/13543776.5.7.653
    37. J. Buckingham. A. 1995, 1-30. https://doi.org/10.1007/978-1-4899-3316-4_1
    38. Peter C Bates, Philip W Ledger, Roger Aston. Overview Anti-infectives: Recent advances in the treatment of septic shock. Expert Opinion on Therapeutic Patents 1994, 4 (8) , 917-930. https://doi.org/10.1517/13543776.4.8.917
    39. Min Chu, Ronald Mierzwa, Imbi Truumees, Frank Gentile, Mahesh Patel, Vincent Gullo, Tze-Ming Chan, Mohindar S. Puar. Two novel diketopiperazines isolated from the fungus Tolypocladium sp.. Tetrahedron Letters 1993, 34 (47) , 7537-7540. https://doi.org/10.1016/S0040-4039(00)60393-3
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1992, 57, 22, 5817–5818
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo00048a008
    Published October 1, 1992
    Request reuse permissions

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