Total Synthesis of (±)‐Strictamine |
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Authors: | Dr. Weiwu Ren Dr. Qian Wang Prof. Dr. Jieping Zhu |
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Affiliation: | 1. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, Lausanne, Switzerland;2. http://lspn.epfl.ch |
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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. |
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Keywords: | alkaloids cyclization heterocycles natural products total synthesis |
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