Journal article
Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine
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Author list: Córdova, Armando
Publication year: 2012
Start page: 398
End page: 408
Number of pages: 11
ISSN: 1434-193X
DOI: http://dx.doi.org/10.1002/ejoc.201101296
View additional information: View in Web of Science™
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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