Synthesis of indolizidines (−)-195B, (−)-223AB and (−)-239AB: (2S,5R)-1-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4-pentenyl)pyrrolidine as a versatile chiral building block

✍ Scribed by Catherine Célimène; Hamid Dhimane; Gérard Lhommet

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 782 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00498-0

✦ Synopsis

The total syntheses of three levogyre 3,5-disubstituted indolizidines, (-)-195B, (-)-223AB and (-)-239AB are described. The employed strategy is based on the utilization of the common enantiopure trans 2,5-disubstituted pyrrolidine 3, which is assembled by addition of pent-4-enylcopper to N-acyl iminium ion derived from (S)-proline.