Multicomponent Linchpin Coupling of Silyl Dithianes Employing an N-Ts Aziridine as the Second Electrophile:  Synthesis of (−)-Indolizidine 223AB

Amos B. Smith, III* and Dae-Shik Kim
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104
Org. Lett., 2004, 6 (9), pp 1493–1495
DOI: 10.1021/ol049601b
Publication Date (Web): March 31, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, smithab@sas.upenn.edu

Abstract

Abstract Image

An efficient, stereocontrolled assembly of the indolizidine alkaloid, (−)-indolizidine 223AB, exploiting a three-component linchpin coupling employing an N-Ts aziridine as the second electrophile, followed by a one-pot sequential construction of the indolizidine ring system, has been achieved. The longest linear sequence was 10 steps, proceeding in 10% overall yield.

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History

  • Published In Issue April 29, 2004
  • Received March 3, 2004

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