doi: 10.1021/jo035522m.
First total synthesis of 1-O-beta-D-glucopyranosyl-5-deoxyadenophorine and its aglycon congener: determination of the absolute configuration
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- PMID: 14987003
- DOI: 10.1021/jo035522m
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First total synthesis of 1-O-beta-D-glucopyranosyl-5-deoxyadenophorine and its aglycon congener: determination of the absolute configuration
J Org Chem.
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Abstract
The first total synthesis of the potent glycosidase inhibitors 1-O-beta-D-glucopyranosyl-5-deoxyadenophorine and its aglycon congener is described in respectively 13 steps (9% overall yield) and 9 steps (29% overall yield) from (R)-Garner aldehyde. The synthesis takes advantage of several key reactions including a diastereoselective allylation of a chiral imine, a stereoselective epoxidation, and a glycoside coupling. In addition this study established unambiguously the absolute configuration of the natural products.
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