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A concise synthesis of castanospermine by the use of a transannular cyclization.

The Journal of organic chemistry (2009-10-28)
Thomas Jensen, Mette Mikkelsen, Anne Lauritsen, Thomas L Andresen, Charlotte H Gotfredsen, Robert Madsen
RESUMEN

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.

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Sigma-Aldrich
(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 98%