Diterpene chemistry. VI. Some chemistry of 8,14-epoxypimaric acid. Comments on the biosynthesis of tetracyclic diterpenes
作者:
John W. ApSimon,
Steven F. Hall,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1978)
卷期:
Volume 56,
issue 16
页码: 2156-2162
ISSN:0008-4042
年代: 1978
DOI:10.1139/v78-352
出版商: NRC Research Press
数据来源: NRC
摘要:
The cleavage of methyl pimarate 8,(14) α-epoxide (4) was studied with a variety of acidic reagents. The major products observed were the corresponding Δ7,8-14α-alcohol and dienes. Participation of the vinyl group was not detected.Consideration of the stereoelectronic requirements for cyclisation of olefins with carbonium ions at C-8 of the pimarane skeleton suggest that the pimaranes are not the biogenetic precursors of the tetracyclic diterpenes. A modification of the traditional route is presented as a working hypothesis.
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