ScholarLens Back to search
2007•The Journal of Organic ChemistryRequires access

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

Open publisher page 39 citations

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.

About this research paper

What this paper is about

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.

Why it matters

OpenAlex reports 39 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available 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.

Key concepts: Enantiopure drug, Pyrrolizidine, Chemistry, Indolizidine, Stereochemistry, Swainsonine, Proline, Total synthesis

Related papers

Related paper 1Related paper 2Related paper 3
Back to paper searchBrowse research topicsOriginal source
New Access to Indolizidine and Pyrrolizidine Alkaloids from an Enantiopure Proline: Total Syntheses of (−)-Lentiginosine and (1R,2R,7aR)-Dihydroxypyrrolizidine — Research Paper | ScholarLens