Total Synthesis of (-)-Isopisiferin: Confirmation of Absolute Configuration

Starting from 4,4‐dimethyl‐2‐cyclohexenone, an enantioselective synthesis of (–)‐isopisiferin has been accomplished in 15 steps with an overall yield of 11.4 %. This work not only provides synthetic evidence for confirming the absolute configuration of natural isopisiferin itself, but also serves as...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2010-08, Vol.2010 (22), p.4271-4275
Main Authors: Jan, Ning-Wei, Liu, Hsing-Jang, Hsieh, Min-Tsang, Shia, Kak-Shan
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Configuration determination
Enantioselectivity
Exact sciences and technology
Lithium
Natural products
Organic chemistry
Preparations and properties
Terpenoids
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Summary:Starting from 4,4‐dimethyl‐2‐cyclohexenone, an enantioselective synthesis of (–)‐isopisiferin has been accomplished in 15 steps with an overall yield of 11.4 %. This work not only provides synthetic evidence for confirming the absolute configuration of natural isopisiferin itself, but also serves as an additional correlation origin to which many related icetexane‐type diterpenes, particular for the pisiferin family, can be referred. Starting from 4,4‐dimethyl‐2‐cyclohexenone, an enantioselective synthesis of (–)‐isopisiferin has been accomplished in 15 steps with an overall yield of 11.4 %.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201000449