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

DOI: 10.1016/S0040-4020(97)01029-6

Source and publish data:

Tetrahedron p. 16471 - 16488 (1997)

Update date:2022-08-12

Topics:

Authors:

Yang, Hong Woon

Zhao, Cunxiang

Romo, Daniel

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Article abstract of DOI:10.1016/S0040-4020(97)01029-6

A concise and highly diastereoselective route to β-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.

Full text of DOI:10.1016/S0040-4020(97)01029-6

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