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1: Org Lett. 2006 Jul 6;8(14):3069-72.Click here to read Links

Stereodivergent syntheses of conduramines and aminocyclitols.

Alegret C, Benet-Buchholz J, Riera A.

Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institut de Recerca Biomédica (IRB), and Departament de Química Orgànica, Universitat de Barcelona, Parc Científic de Barcelona, Spain.

[reaction: see text] 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).

PMID: 16805554 [PubMed - indexed for MEDLINE]