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Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

โœ Scribed by Smith, Adrian L.; Williams, Simon F.; Holmes, Andrew B.; Hughes, Leslie R.; Swithenbank, Colin.; Lidert, Zev.

Book ID
120420754
Publisher
American Chemical Society
Year
1988
Tongue
English
Weight
442 KB
Volume
110
Category
Article
ISSN
0002-7863

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Enantioselective synthesis of (โˆ’)-indoli
Enantioselective synthesis of (โˆ’)-indolizidine 167B
โœ Pierre Chalard; Roland Remuson; Yvonne Gelas-Mialhe; Jean-Claude Gramain; Isabel ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 187 KB

The enantioselective total synthesis of (-)-indolizidine 167B is described. The key step is the intramolecular cyclization of the chiral N-acyliminium ion 6. Indolizidine 167B was obtained in 7 steps and 17% yield from ethyl (R)-3-aminohexanoate, with an enantiomeric excess of 93%.