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Acylnitrilium ion-initiated heteroannulations in alkaloid synthesis. An efficient, stereocontrolled, total synthesis of the Orchidaceae alkaloid (.+-.)-dendrobine

CH Lee, M Westling, T Livinghouse…

文献索引:Lee, Cheol Hae; Westling, Mark; Livinghouse, Tom; Williams, Andrew C. Journal of the American Chemical Society, 1992 , vol. 114, # 11 p. 4089 - 4095

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被引用次数: 40

摘要

Abstract: A concise total synthesis of (A)-dendrobine is described that proceeds in eight steps from 2-methylcyclopent-2-en-1-one. The key transformation in this approach is the silver ion mediated cyclocondensation of the isonitrile 6 with the acyl chloride 5. This highly convergent reaction proceeds in excellent (88%) overall yield to provide the AI-pyrroline 4.