Biosynthetically Inspired Divergent Approach to Monoterpene Indole Alkaloids: Total Synthesis of Mersicarpine, Leuconodines B and D, Leuconoxine, Melodinine E, Leuconolam, and Rhazinilam

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• 作者：Yang Yang ; Yu Bai ; Siyuan Sun ; Mingji Dai
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：December 5, 2014
• 年：2014
• 卷：16
• 期：23
• 页码：6216-6219
• 全文大小：406K
• ISSN：1523-7052

文摘

Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop鈥揥interfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.