Asymmetric Synthesis of anti-Aldol Segments via a Nonaldol Route: Synthetic Applications to Statines and (-)-Tetrahydrolipstatin

作者：Ghosh Arun K^*; Shurrush Khriesto; Kulkarni Sarang

来源：Journal of Organic Chemistry, 2009, 74(12): 4508-4518.

DOI：10.1021/jo900642f

An asymmetric synthesis of anti-aldol segments via a nonaldol route is described. The strategy involves a highly diastereoselective synthesis of functionalized tetrahydrofuran derivatives from optically active 4-phenylbutyrolactone. Treatment of the tetrahydrofuran derivatives with a Lewis acid and acetic anhydride provided the corresponding ring-opened styrene derivatives. Oxidative cleavage of the styrene derivatives provided access to the anti-aldol segments. The utility of this methodology was demonstrated by the synthesis of statine derivatives and pancreatic lipase inhibitor, (-)-tetrahydrolipstatin.

• 出版日期2009-6-19