Reduction of lactams and thiolactams by sodium borohydride. Application in the synthesis of some alkaloids

…, VS Giri, MS Sabeena, SC Pakrashi

文献索引：Mandal, S. B.; Giri, V. S.; Sabeena, M. S.; Pakrashi, S. C. Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4236 - 4241

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被引用次数: 52

摘要

Lactams la-8a and thiolactams lb-8b, 9a, 10b-l2b, and 13 could be reduced to their corresponding amines in 70-98% yield by using sodium borohydride-tert-butyl alcohol- methanol mixtures under reflux. Even the vinylogous amide 19 underwent reduction to afford deplancheine (18) in 53% yield. The use of this reagent has also been extended to the synthesis of bharatamine (loa), aspidospermidine (12d), and quebrachamine (17).