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Total Synthesis of (±)‐Strictamine
Author(s) -
Ren Weiwu,
Wang Qian,
Zhu Jieping
Publication year - 2016
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.201511638
Subject(s) - stereocenter , intramolecular force , ketone , amine gas treating , trifluoromethanesulfonate , chemistry , nucleophilic substitution , total synthesis , tertiary amine , enol , quaternary carbon , nucleophile , halogenation , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
The total synthesis of strictamine has been achieved in nine steps from a known enol triflate. Characteristic features of our approach included: a) creation of a C7 all‐carbon quaternary stereocenter at an early synthetic stage; b) use of an N,N‐dimethyl tertiary amine as a surrogate of the primary amine for the rapid build‐up of a functionalized 2‐azabicyclo[3,3,1]nonan‐9‐one skeleton (achieved by using a reaction sequence of α‐bromination of the ketone, followed by a stereoconvergent intramolecular nucleophilic substitution reaction); and c) a late‐stage construction of the indolenine unit.