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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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