Enantiodivergent Total Syntheses of (+)- and (-)-Scopadulcic Acid A

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• 作者：Martin E. Fox ; Chi Li ; Joseph P. Marino ; Jr. ; and Larry E. Overman
• 刊名：Journal of the American Chemical Society
• 出版年：1999
• 出版时间：June 16, 1999
• 年：1999
• 卷：121
• 期：23
• 页码：5467 - 5480
• 全文大小：229K
• 年卷期：v.121,no.23(June 16, 1999)
• ISSN：1520-5126

文摘

The first enantioselective total synthesis of scopadulcic acid A is described. The key step is a cascadeintramolecular Heck reaction of a methylenecycloheptene iodide, which generates the B, C, and D rings of thescopadulan ring system in 90% yield as a single stereoisomer. A distinctive feature of these syntheses is theuse of stereoselective enolization to dictate which enantiomer of the natural product is produced.