Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 10, Pages 3500-3503Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511638
Keywords
alkaloids; cyclization; heterocycles; natural products; total synthesis
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
- Swiss National Centres of Competence in Research (NCCR-Chem Biol)
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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 -bromination of the ketone, followed by a stereoconvergent intramolecular nucleophilic substitution reaction); and c)a late-stage construction of the indolenine unit.
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