Total Synthesis of Solandelactones E and F, Homoeicosanoids from the Hydroid Solanderia secunda

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• 作者：James D. White ; William H. C. Martin ; Christopher Lincoln ; Jongtae Yang
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：August 16, 2007
• 年：2007
• 卷：9
• 期：17
• 页码：3481 - 3483
• 全文大小：71K
• 年卷期：v.9,no.17(August 16, 2007)
• ISSN：1523-7052

文摘

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Asymmetric total syntheses of solandelactones E and F confirmed that hydroxyl configuration at C11 in these oxylipins had been misassignedand that the stereochemistry at this center should be reversed. Key steps in the synthesis involved a Nagao asymmetric acetate aldol reaction,a directed Simmons-Smith cyclopropanation, a Holmes-Claisen rearrangement to establish the unsaturated octalactone, and a Nozaki-Hiyama-Kishi coupling to connect two major fragments at C11-C12.