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Total synthesis of biselides A and B

DOI

Bibliographic Information

Other Title
  • 海洋産ポリケチド ビセライドA・Eの全合成

Abstract

<p>Biselides, oxygenated analogues of haterumalides, were isolated from the Okinawan ascidian Didemnidae sp. by our group. Biselides A (1), B (2) and haterumalide NA methyl ester showed stronger cytotoxicity than did the anticancer drug cisplatin against various human cancer cells. In contrast, these compounds exhibited no toxicity against brine shrimp. These results suggested that haterumalides and biselides could become lead compounds of novel-type anticancer drugs without severe side effects. The structure of biselide E (7) is different from other biselides, and has a conjugated six-membered lactone. The biological activity of biselide E (7) has never been studies so far, due to lack of samples for biological evaluations. Thus, we planned the practical synthesis of biselides based on our synthetic route of haterumalides. </p><p>Common intermediate for biselides (20) was prepared by enzymatic regioselective hydrolysis for the introduction of C20 oxygen functional group. Biselide A (1) was synthesized from this common intermediate by using asymmetric aldol reaction, as a key step. Also, we achieved the total synthesis of biselide E (7). The highlight of this synthesis is the construction of a conjugated six-membered lactone from b-chloroacetoxy-d-lactone derivative 46 at the late stage of total synthesis. </p>

Journal

Details

  • CRID
    1390845702294186368
  • NII Article ID
    130007722882
  • DOI
    10.24496/tennenyuki.58.0_oral5
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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