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

Publication: Research - peer-reviewJournal article – Annual report year: 2009

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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
Publication date2009
Volume74
Issue22
Pages8886-8889
ISSN0022-3263
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 17
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