The Journal of Organic Chemistry

Synthesis of 2 (R), 5 (R)-bis (hydroxymethyl)-3 (R), 4 (R)-dihydroxypyrrolidine. A novel glycosidase inhibitor

PJ Card, WD Hitz

Index: Card, Peter J.; Hitz, William D. Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 891 - 893

Full Text: HTML

Citation Number: 55

Abstract

Pyrrolidine 3 with absolute configuration as indicated represents a challenging synthetic target because of its four contiguous asymmetric centers. We chose L-sorbose as our starting material because it contains the desired absolute configuration at C-3 and C-4 and the opposite configuration at C-5 that would be inverted upon substitution by a nitrogen nucleophile. Subsequent ring closure via attack of the nitrogen upon C-2 followed by ...