Org Lett. 2003 Aug 21;5(17):3001-4.

New stereodivergent approach to 3-amino-2,3,6-trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epi-daunosamine.

Ginesta X, Pastó M, Pericàs MA, Riera A.

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Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Departament de Química Orgànica/Parc Científic de Barcelona, Universitat de Barcelona, C/Josep Samitier 1-5, 08028 Barcelona, Spain.

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.

PMID:: 12916966; [PubMed - indexed for MEDLINE]

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