Synthesis of endrin metabolites. Part 2: Total synthesis and confirmation of the structure of 3‐hydroxyendrin
作者:
Colin T. Bedford,
Anthony E. Crane,
Edward H. Smith,
Nicholas K. Wellard,
期刊:
Pesticide Science
(WILEY Available online 1986)
卷期:
Volume 17,
issue 1
页码: 33-47
ISSN:0031-613X
年代: 1986
DOI:10.1002/ps.2780170105
出版商: John Wiley&Sons, Ltd
数据来源: WILEY
摘要:
Abstract3‐Hydroxyendrin, a minor metabolite of endrin in several mammals, has been synthesised for the first time in a three‐step procedure. The synthesis is based on the two‐step commercial manufacture of endrin, with cyclopenta‐1,3‐dienyl acetate replacing cyclopentadiene in the Diels‐Alder adduction step to isodrin formation. The adduct formed from cyclopenta‐1,3‐dienyl acetate and 1,2,3,4,7,7‐hexachlorobicyclo‐[2.2.1]hepta‐2,5‐diene, 3‐acetoxyisodrin, was purified by chromatography and sequentially deacetylated (to 3‐hydroxyisodrin) and epoxidised to yield 3‐hydroxyendrin. A comparison of this material with a sample of a metabolite, isolated from endrin‐dosed rates in 1970, showed that they were identical in all spectral properties (m.s., i.r. and n.m.r.). This has provided confirmation of the original structural assignment and has made available sufficient quantities of the metabolite as a reference material for any futur
点击下载:
PDF
(576KB)
返 回