THE FIRST TOTAL SYNTHESIS OF (-)-LIPSTATIN

Authors
POMMIER A PONS JM KOCIENSKI PJ
Citation
A. Pommier et al., THE FIRST TOTAL SYNTHESIS OF (-)-LIPSTATIN, Journal of organic chemistry, 60(22), 1995, pp. 7334-7339
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
22
Year of publication
1995
Pages
7334 - 7339
Database
ISI
SICI code
0022-3263(1995)60:22<7334:TFTSO(>2.0.ZU;2-X
Abstract
A key step in the first total synthesis of the potent pancreatic lipas e inhibitor (-)-lipstatin (1) is a diastereoselective Lewis acid-promo ted [2 + 2] cycloaddition reaction between n-hexyl(trimethylsilyl)kete ne (4) and -[(tert-butyldimethylsilyl)oxy]5,8-tetradecadienal (3), whi ch is prepared from dimethyl (S)-(-)-malate.