Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 49, Pages 14937-14940Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508150
Keywords
alkaloids; cyclizations; heterocycles; natural products; total synthesis
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Funding
- EPFL (Switzerland)
- Swiss State Secretariat for Education and Research (SER)
- Swiss National Science Foundation (SNSF)
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A concise enantioselective total synthesis of (-)-isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N-Alkylation of an enantio- enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of pivalic acid, was converted into the hexacyclic structure of natural product by a complex but ordered domino sequence. The one-pot process leading to the formation of one C-C bond and three C-N bonds created three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry.
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