Journal article
A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization
In
Journal of Organic Chemistry
—
2009, Volume 74, Issue 22, pp. 8886-8889
From
Department of Chemistry, Building 201, Technical University of Denmark, DK-2800 Lyngby, Denmark
Abstract
A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl α-d-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the natural product.
| Language: | English |
|---|---|
| Publisher: | American Chemical Society |
| Year: | 2009 |
| Pages: | 8886-8889 |
| ISSN: | 15206904 and 00223263 |
| Types: | Journal article |
| DOI: | 10.1021/jo9019495 |
