Stereodivergent syntheses of conduramines and aminocyclitols.
[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).
Alegret
Carlos
C
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.
Benet-Buchholz
Jordi
J
Riera
Antoni
A
D003511:Cyclohexanols / Q000138:chemical synthesis*; D053138:Cyclohexenes / Q000138:chemical synthesis*; D003514:Cyclohexylamines / Q000138:chemical synthesis*; D006595:Hexosamines / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D003511:Cyclohexanols; D053138:Cyclohexenes; D003514:Cyclohexylamines; D006595:Hexosamines