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

Authors
YANG HW ZHAO CX ROMO D
Citation
Hw. Yang et al., 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, Tetrahedron, 53(48), 1997, pp. 16471-16488
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
48
Year of publication
1997
Pages
16471 - 16488
Database
ISI
SICI code
0040-4020(1997)53:48<16471:SOTTMA>2.0.ZU;2-O
Abstract
A concise and highly diastereoselective route to beta-lactones has bee n 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 met hodology. Recent optimization and extensions of this method are descri bed which include variation of the silyl group and leaving group of th e ketene acetal. (C) 1997 Elsevier Science Ltd.