X. Ginesta, Mireia Pastó, M. A. Pericàs
Jul 19, 2003
Citations
0
Influential Citations
36
Citations
Journal
Organic letters
Abstract
[reaction: see text] An enantioselective preparation of the four diastereomeric 3-amino-2,3,6-trideoxy-hexoses, key components of anthracycline antibiotics, has been developed. Sharpless catalytic asymmetric epoxidation of the (2E)-2,5-hexadien-1-ol, regioselective ring opening with azide, followed by convenient functional group transformations, afforded the key aldehydes cis- or trans-6 in any configuration. The diastereoselective addition of methylmetal reagents to these aldehydes followed by ozonolysis gives access in a completely stereocontrolled manner to the four isomeric trideoxyaminosugars.