Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one

P. Armstrong, G. O'Mahony, Paul Stevenson, A.D. Walker

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Catalytic hydrogenation of dihydroindolizidinone occurred preferentially from the endo-face giving rapid entry to (8R,8aS)-8-methylhexahydroindolizin-5-one, a key intermediate in the synthesis of 5,8-disubstituted indolizidines and deoxypumiliotoxin 25 1 H. The selectivity could be improved further by diimide reduction though this also resulted in some oxidation of the alkene to the diene. The basis of the unusual stereoselectivity in the diimide reduction is believed to be stereoelectronic in origin. (c) 2005 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)8109-8111
Number of pages3
JournalTetrahedron Letters, ISSN
Volume46
Issue number47
DOIs
Publication statusPublished - 21 Nov 2005

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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