Sulfoxide-Mediated Asymmetric Synthesis of Glycosidase Inhibitor
Precursors

Bueno, Ana B.; Carreño, M. Carmen; L. García Ruano, José; Arrayás, Ramón Gómez; Zarzuelo, María M.

doi:10.1021/jo961774u.s001

Sulfoxide-Mediated Asymmetric Synthesis of Glycosidase Inhibitor Precursors

journal contribution

posted on 1997-04-04, 00:00 authored by Ana B. Bueno, M. Carmen Carreño, José L. García Ruano, Ramón Gómez Arrayás, María M. Zarzuelo

The highly diastereoselective DIBALH and DIBALH/ZnBr₂ 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.