American Chemical Society
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Stereodivergent Syntheses of Conduramines and Aminocyclitols

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posted on 2006-07-06, 00:00 authored by Carlos Alegret, Jordi Benet-Buchholz, Antoni Riera
The diastereomers of 6-amino-cyclohex-3-ene-1,2-diols 1 (4-deoxy-3-conduramines), key building blocks for the syntheses of a large range of natural products, have been enantioselectively prepared. Diastereoselective dihydroxylation of the compounds provided a new family of aminocyclitols 2 (deoxyinosamines). The key reactions of our syntheses are Sharpless catalytic asymmetric epoxidation, diastereoselective addition of vinylmetal reagents to the aldehydes, and ring-closing metathesis (RCM).