New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline: total syntheses of (-)-lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine

Steven R Angle; David Bensa; Dominique S Belanger

doi:10.1021/jo070462w

New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline: total syntheses of (-)-lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine

J Org Chem. 2007 Jul 20;72(15):5592-7. doi: 10.1021/jo070462w. Epub 2007 Jun 28.

Authors

Steven R Angle¹, David Bensa, Dominique S Belanger

Affiliation

¹ Department of Chemistry, University of California, Riverside, CA 92521-0403, USA. [email protected]

PMID: 17602588
DOI: 10.1021/jo070462w

Abstract

A new approach to the synthesis of indolizidine and pyrrolizidine skeletons is reported. (-)-Lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine have both been synthesized in 13 steps from di-O-isopropylidene-d-mannitol. The common key intermediate is (-)-dihydroxyproline benzyl ester 10.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Proline / chemistry*
Pyrrolizidine Alkaloids / chemical synthesis*
Pyrrolizidine Alkaloids / chemistry
Spectrometry, Mass, Fast Atom Bombardment
Stereoisomerism

Substances

Alkaloids
Pyrrolizidine Alkaloids
lentiginosine
Proline