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Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine

✍ Scribed by Shuangzheng Lin; Luca Deiana; Abrehet Tseggai; Armando Córdova

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 747 KB
Volume: 2012
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201101296

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✦ Synopsis

Abstract

A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one‐pot three‐component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (–)‐dihydrocorynanthenol, (–)‐protoemetinol, (–)‐protoemetine, (–)‐3‐epi‐protoemetinol, and emetine (3–6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One‐pot three‐component highly enantioselective catalytic Michael/Pictet–Spengler/lactamization cascade reactions; (ii) One‐pot tandem Swern oxidation/Wittig sequences; (iii) One‐pot tandem hydrogenation sequences.

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