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Three unprecedented chloro steroids from the Maui sponge Strongylacidon sp.: kiheisterones C, D, and E

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    Three unprecedented chloro steroids from the Maui sponge Strongylacidon sp.: kiheisterones C, D, and E
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1993, 58, 12, 3460–3462
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    https://doi.org/10.1021/jo00064a041
    Published June 1, 1993
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    Cited By

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    This article is cited by 20 publications.

    1. Liping Huo, Xiaofang Li, Yaheng Zhao, Ling Li, Lingling Chu. Site- and Stereoselective Synthesis of Alkenyl Chlorides by Dual Functionalization of Internal Alkynes via Photoredox/Nickel Catalysis. Journal of the American Chemical Society 2023, 145 (17) , 9876-9885. https://doi.org/10.1021/jacs.3c02748
    2. Hao Cui, Yang Shen, Yanyu Chen, Ruifeng Wang, Haoxiang Wei, Pengfei Fu, Xin Lei, Haoxiang Wang, Ruihao Bi, Yandong Zhang. Two-Stage Syntheses of Clionastatins A and B. Journal of the American Chemical Society 2022, 144 (20) , 8938-8944. https://doi.org/10.1021/jacs.2c03872
    3. Wei Ju, Xudong Wang, Hailong Tian, Jinghan Gui. Asymmetric Total Synthesis of Clionastatins A and B. Journal of the American Chemical Society 2021, 143 (33) , 13016-13021. https://doi.org/10.1021/jacs.1c07511
    4. Nittala S. Sarma, Moturi S. Krishna, Sk. Gouse Pasha, Thota S. Prakasa Rao, Y. Venkateswarlu and P. S. Parameswaran. Marine Metabolites: The Sterols of Soft Coral. Chemical Reviews 2009, 109 (6) , 2803-2828. https://doi.org/10.1021/cr800503e
    5. Ernesto Fattorusso,, Orazio Taglialatela-Scafati,, Francesca Petrucci,, Giorgio Bavestrello,, Barbara Calcinai,, Carlo Cerrano,, Paola Di Meglio, and, Angela Ianaro. Polychlorinated Androstanes from the Burrowing Sponge Cliona nigricans. Organic Letters 2004, 6 (10) , 1633-1635. https://doi.org/10.1021/ol049548r
    6. Gordon W. Gribble. Naturally Occurring Organohalogen Compounds. Accounts of Chemical Research 1998, 31 (3) , 141-152. https://doi.org/10.1021/ar9701777
    7. Valery M. Dembitsky. Chemical Diversity of Ketosteroids as Potential Therapeutic Agents. Microbiology Research 2024, 15 (3) , 1516-1575. https://doi.org/10.3390/microbiolres15030103
    8. Valery M. Dembitsky. Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms. Molecules 2023, 28 (14) , 5549. https://doi.org/10.3390/molecules28145549
    9. Hao Cui, Yang Shen, Ruifeng Wang, Haoxiang Wei, Xin Lei, Yanyu Chen, Pengfei Fu, Haoxiang Wang, Ruihao Bi, Yandong Zhang. Synthesis of Clionastatins A and B through Enhancement of Chlorination and Oxidation Levels of Testosterone. Chinese Journal of Chemistry 2022, 40 (23) , 2747-2755. https://doi.org/10.1002/cjoc.202200425
    10. Jean‐Michel Kornprobst. Porifera (Sponges)–1. 2014, 607-703. https://doi.org/10.1002/9783527335855.marprod019
    11. Jean‐Michel Kornprobst. Porifera (Sponges)–5. 2014, 951-1086. https://doi.org/10.1002/9783527335855.marprod195
    12. Alla G. Guzii, Tatyana N. Makarieva, Vladimir A. Denisenko, Pavel S. Dmitrenok, Yuliya V. Burtseva, Vladimir B. Krasokhin, Valentin A. Stonik. Topsentiasterol sulfates with novel iodinated and chlorinated side chains from the marine sponge Topsentia sp.. Tetrahedron Letters 2008, 49 (50) , 7191-7193. https://doi.org/10.1016/j.tetlet.2008.10.007
    13. Xiao-Hong Yan, Li-Ping Lin, Jian Ding, Yue-Wei Guo. Methyl spongoate, a cytotoxic steroid from the Sanya soft coral Spongodes sp.. Bioorganic & Medicinal Chemistry Letters 2007, 17 (9) , 2661-2663. https://doi.org/10.1016/j.bmcl.2007.01.095
    14. Nittala S. Sarma, M. Sri Rama Krishna, S. Ramakrishna Rao. Sterol Ring System Oxidation Pattern in Marine Sponges. Marine Drugs 2005, 3 (3) , 84-111. https://doi.org/10.3390/md303084
    15. Enrique Dorta, Ana R. Dı́az-Marrero, Mercedes Cueto, Luis D’Croz, Juan L. Maté, Aurelio San-Martı́n, José Darias. Unusual chlorinated pregnanes from the eastern Pacific octocoral Carijoa multiflora. Tetrahedron Letters 2004, 45 (5) , 915-918. https://doi.org/10.1016/j.tetlet.2003.11.113
    16. Makoto Iwashima, Ken Nara, Yoshiyuki Nakamichi, Kazuo Iguchi. Three new chlorinated marine steroids, yonarasterols G, H and I, isolated from the Okinawan soft coral, Clavularia viridis. Steroids 2001, 66 (1) , 25-32. https://doi.org/10.1016/S0039-128X(00)00144-6
    17. Gerhard Laus. Biological activities of natural halogen compounds. 2001, 757-809. https://doi.org/10.1016/S1572-5995(01)80022-3
    18. J. Buckingham. C. 1995, 42-77. https://doi.org/10.1007/978-1-4899-3316-4_3
    19. Paul J. Scheuer. From the rainforest to the reef: Searching for bioactive natural products in the mid‐pacific. Medicinal Research Reviews 1994, 14 (5) , 487-503. https://doi.org/10.1002/med.2610140502
    20. H. Shimura, K. Iguchi, Y. Yamada, S. Nakaike, T. Yamagishi, K. Matsumoto, C. Yokoo. Aragusterol C: A novel halogenated marine steroid from an Okinawan sponge,Xestospongia sp., possessing potent antitumor activity. Experientia 1994, 50 (2) , 134-136. https://doi.org/10.1007/BF01984951
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1993, 58, 12, 3460–3462
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo00064a041
    Published June 1, 1993
    Request reuse permissions

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