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An improved synthesis of (−)-syringolides and X-ray structural characterization of synthetic (−)-syringolide 1

✍ Scribed by Pei Yu; Qi-Guang Wang; Thomas C.W. Mak; Henry N.C. Wong

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
345 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

On treatment with 10% HF, butenolides 4a and 4b afforded enantiopure (-)-syringolides 1 (la) and 2 (lb) respectively in much higher yields. Unprecedentedly, the cyclic acetal 5a was also converted to la by reacting with an excess of p-TsOH. The structure of the ~ynthetic (-)-syringolide 1 (la) was substantiated by an X-ray crystallographic study.

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