Sulfoxide-Mediated Asymmetric Synthesis of Glycosidase Inhibitor Precursors.
The highly diastereoselective DIBALH and DIBALH/ZnBr(2) reduction of enantiomerically pure (5S,(S)S)-3-ethoxy-5-(p-tolylsulfinyl)cyclopentenone (9) is used as a key step to the synthesis of oxazolidinone 2, a precursor of glycosidase inhibitor mannostatin. Compound 9 was obtained from 3-ethoxycyclopentenone by direct sulfinylation with (S)-N-benzyl-N-(p-tolylsulfinyl)propionamide.
Bueno
Ana B.
AB
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
Carreño
M. Carmen
MC
García Ruano
José L.
JL
Arrayás
Ramón Gómez
RG
Zarzuelo
María M.
MM