A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization

Thomas Jensen, Mette Mikkelsen, Anne Lauritsen, Thomas Lars Andresen, Charlotte Held Gotfredsen, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-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.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume74
Issue number22
Pages (from-to)8886-8889
ISSN0022-3263
DOIs
Publication statusPublished - 2009

Fingerprint Dive into the research topics of 'A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization'. Together they form a unique fingerprint.

Cite this