Stereoselective synthesis and biological evaluation of d-fagomine, d-3-epi-fagomine and d-3,4-epi-fagomine analogs from d-glyceraldehyde acetonide as a common building block?

Organic & Biomolecular Chemistry Pub Date: 2012-10-11 DOI: 10.1039/C2OB26732B

Abstract

The stereoselective synthesis of D-fagomine, D-3-epi-fagomine, and D-3-epi-fagomine analogs starting from readily available D-glyceraldehyde acetonide has been achieved. The synthesis involves diastereoselective anti-vinylation of its homoallylimine, ring-closing metathesis, and stereoselective epoxidation followed by regioselective ring-opening or stereoselective dihydroxylation. The lack of a strong activity as glycosidase inhibitors of these compounds could be advantageous for their therapeutic use as chaperones.

Graphical abstract: Stereoselective synthesis and biological evaluation of d-fagomine, d-3-epi-fagomine and d-3,4-epi-fagomine analogs from d-glyceraldehyde acetonide as a common building block
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