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General Entry to Aspidosperma Alkaloids: Enantioselective Total Synthesis of (−)‐Aspidophytine
Author(s) -
Yang Rongwen,
Qiu Fayang G.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302442
Subject(s) - enantioselective synthesis , total synthesis , aspidosperma , pyrrolidine , computer science , service (business) , combinatorial chemistry , chemistry , stereochemistry , operations research , organic chemistry , mathematics , business , indole test , marketing , catalysis
A general approach toward the asymmetric total synthesis of various aspidosperma alkaloids includes the combination of a CH bond activation with a Heck‐type coupling, and the stereo‐controlled formation of piperidine and pyrrolidine rings as key steps. The feasibility of this approach was demonstrated with the total synthesis of aspidophytine in 18 steps from 4,4‐disubstituted cyclohexanedione and 2,3‐dimethoxyaniline (see scheme).