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

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

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被引用次数: 55

摘要

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 ...