Total Synthesis of (±)-Strictamine
- PMID:26845231
- DOI: 10.1002/anie.201511638
Total Synthesis of (±)-Strictamine
Abstract
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.
Keywords: alkaloids; cyclization; heterocycles; natural products; total synthesis.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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