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Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3‐ epi ‐Protoemetinol and Emetine
Author(s) -
Lin Shuangzheng,
Deiana Luca,
Tseggai Abrehet,
Córdova Armando
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101296
Subject(s) - chemistry , enantioselective synthesis , tryptamine , swern oxidation , total synthesis , cascade reaction , tandem , michael reaction , stereochemistry , emetine , combinatorial chemistry , catalysis , organic chemistry , biochemistry , medicine , materials science , pharmacology , dimethyl sulfoxide , composite material
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.