Journal
ORGANIC LETTERS
Volume 16, Issue 23, Pages 6216-6219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503150c
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- Purdue University
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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-Winterfeldt 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.
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