AN IMPROVED SYNTHESIS OF (-)-SYRINGOLIDES AND X-RAY STRUCTURAL CHARACTERIZATION OF SYNTHETIC (-)-SYRINGOLIDE-1

Authors
YU P WANG QG MAK TCW WONG HNC
Citation
P. Yu et al., AN IMPROVED SYNTHESIS OF (-)-SYRINGOLIDES AND X-RAY STRUCTURAL CHARACTERIZATION OF SYNTHETIC (-)-SYRINGOLIDE-1, Tetrahedron, 54(9), 1998, pp. 1783-1788
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
9
Year of publication
1998
Pages
1783 - 1788
Database
ISI
SICI code
0040-4020(1998)54:9<1783:AISO(A>2.0.ZU;2-K
Abstract
On treatment with 10% HF, butenolides 4a and 4b afforded enantiopure ( -)-syringolides 1 (1a) and 2 (1b) respectively in much higher yields. Unprecedentedly, the cyclic acetal 5a was also converted to Ire by rea cting with an excess of p-TsOH. The structure of the synthetic (-)-syr ingolide 1 (1a) was substantiated by an X-ray crystallographic study. (C) 1998 Elsevier Science Ltd. All rights reserved.