Total Syntheses of (+)- and (-)-Cacospongionolide B: New Insight into Structural Requirements for Phospholipase A2 Inhibition

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• 作者：Atwood K. Cheung and Marc L. Snapper
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：October 2, 2002
• 年：2002
• 卷：124
• 期：39
• 页码：11584 - 11585
• 全文大小：57K
• 年卷期：v.124,no.39(October 2, 2002)
• ISSN：1520-5126

文摘

The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A₂ suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the -hydroxybutenolide moiety.