A Direct Route to Fluostatin C by a Fascinating Diels-Alder Reaction

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• 作者：Maolin Yu ; Samuel J. Danishefsky
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：March 5, 2008
• 年：2008
• 卷：130
• 期：9
• 页码：2783 - 2785
• 全文大小：87K
• 年卷期：v.130,no.9(March 5, 2008)
• ISSN：1520-5126

文摘

The Diels-Alder reactions between vinylindenes (5 or 6) as the dienes with quinoneketals (7 or 8) or with methacrolein as the dienophiles were investigated. The remarkable regioselectivities of these Diels-Alder adducts suggested that the regiopreferences of these dienes and dienophiles in these cases are not a fixed property of each component of the cycloaddition but are mutually contigent. This paper shows how the Diels-Alder reaction between 6 and 8 was applied to the inaugural total syntheses of fluostatin C and E.