Stereocontrolled Synthesis of the AB Rings of Samaderine C

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• 作者：David J. Burns ; Stefan Mommer ; Peter O鈥橞rien ; Richard J. K. Taylor ; Adrian C. Whitwood ; Shuji Hachisu
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：January 18, 2013
• 年：2013
• 卷：15
• 期：2
• 页码：394-397
• 全文大小：271K
• 年卷期：v.15,no.2(January 18, 2013)
• ISSN：1523-7052

文摘

A concise synthesis of the AB rings of samaderine C (12 steps, 8 isolation steps, 7.8% overall yield), a quassinoid with antifeedant and insecticidal activity, is described. The development of the first general approach to the trans-1,2-diol A-ring motif in samaderine C and other quassinoids is a key feature. The trans-1,2-diol is crafted via stereoselective 伪-hydroxylation (of a silyl enol ether) and reduction, a strategy that has much potential for quassinoid synthesis.