Asymmetric synthesis of the tetrahydropyran ring, C32-C38 fragment, of phorboxazoles.
The asymmetric synthesis of a model aldehyde (2R,6R)-2 and the C32-C38 fragment of phorboxazoles, (2R,4R,6R)-1, is described using a sulfoxide as chiral auxiliary. Key advances include the stereoselective reductions of beta-keto- or beta,gamma-diketosulfoxides, the acid-catalyzed cyclization of enantiopure sulfinyl hydroxy ketone precursors to the tetrahydropyran ring, and the Pummerer reaction on the pendant sulfoxide to create the formyl group.
Brinkmann
Yasmin
Y
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain.
Carreño
M Carmen
MC
Urbano
Antonio
A
Colobert
Françoise
F
Solladié
Guy
G