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Chemistry. 2013 Sep 2;19(36):11847-52. doi: 10.1002/chem.201302669. Epub 2013 Aug 16.

Total synthesis of stemaphylline N-oxide and related c9a-epimeric analogues.

Author information

  • 1Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Station B 351822, Nashville, TN 37235 (USA).

Abstract

Winning the relay: The first total synthesis of stemaphylline N-oxide has been completed utilizing a bistandem relay ring-closing-metathesis (RRCM) strategy, necessitated by the conformation of the requisite tetraene. This effort also gave unnatural 9a-epi-stemaphylline and 9a-epi-stemaphylline N-oxide.

Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

alkaloids; metathesis; stemaphylline; stemaphylline N‐oxide; total synthesis

PMID:
23956045
[PubMed - in process]
PMCID:
PMC3925759
Free PMC Article
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