A novel one-step diastereo- and enantioselective formation of trans-azetidinones and its application to the total synthesis of cholesterol absorption inhibitors

被引：78

作者：

Wu, GZ ^{[1
]}

Wong, YS ^{[1
]}

Chen, X ^{[1
]}

Ding, ZX ^{[1
]}

机构：

[1] Schering Plough Res Inst, Chem Proc Res & Dev, Kenilworth, NJ 07033 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 10期

关键词：

D O I：

10.1021/jo990428k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical asymmetric process was developed for the synthesis of azetidinone-based cholesterol absorption inhibitors. Key to this synthesis was the discovery of a novel one-step diastereo- and enantioselective formation of trans p-lactams starting from commercially available 3(S)-hydroxy-gamma-lactone. Various trans a-lactams can be prepared in good yields and with better than 95:5 enantio- and diastereoselctivity. A Lewis acid-catalyzed aldol condensation and a highly enantioselective oxazaborolidine-catalyzed chiral reduction completes the side chain.

引用

页码：3714 / 3718

页数：5

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