Enantioselective access to 2,7-cis-disubstituted oxepanes: formal synthesis of (+)-isolaurepan.
[reaction: see text] The asymmetric synthesis of 2,7-cis-disubstituted oxepanes bearing a sulfoxide is achieved from commercially available precursors in only five steps. The key step is the highly diastereoselective Et3SiH/TMSOTf-promoted reductive cyclization of enantiopure hydroxysulfinyl aryl or alkyl ketones.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. carmen.carrenno@uam.es
Des Mazery
Renaud
R
Urbano
Antonio
A
Colobert
Françoise
F
Solladié
Guy
G