Total Synthesis of (±)-Strictamine

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 alpha-bromination of the ketone, followed by a stereo convergent intramolecular nucleophilic substitution reaction); and c) a late-stage construction of the indolenine unit.


Published in:
Angewandte Chemie International Edition, 55, 10, 3500-3503
Year:
2016
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
1433-7851
Keywords:
Laboratories:




 Record created 2016-02-27, last modified 2018-12-03


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