Studies of the tandem Mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to beta-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-panclicin D

被引：53

作者：

Yang, HW ^{[1
]}

Zhao, CX ^{[1
]}

Romo, D ^{[1
]}

机构：

[1] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843

来源：

TETRAHEDRON | 1997年 / 53卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(97)01029-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and highly diastereoselective route to beta-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (-) -Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving group of the ketene acetal. (C) 1997 Elsevier Science Ltd.

引用

页码：16471 / 16488

页数：18

共 53 条

[11] STUDIES ON THE TOTAL SYNTHESIS OF LACTACYSTIN - AN IMPROVED ALDOL COUPLING REACTION AND A BETA-LACTONE INTERMEDIATE IN THIOL ESTER FORMATION [J].