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

Journal Article (Journal Article)

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 251H. 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. © 2005 Elsevier Ltd. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Armstrong, P; O'Mahony, G; Stevenson, PJ; Walker, AD

Published Date

  • November 21, 2005

Published In

Volume / Issue

  • 46 / 47

Start / End Page

  • 8109 - 8111

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/j.tetlet.2005.09.133

Citation Source

  • Scopus