Total Synthesis of Absinthin

(+)-Absinthin, a structurally unique triterpene, has been efficiently constructed in nine reaction steps and in 18.6% overall yield from O-acetylisophotosantonic lactone. The synthesis features Mitsunobu arylselenylation, oxidative elimination of allylic arylselenides, biomimetic dimerization via re...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-01, Vol.127 (1), p.18-19
Main Authors: Zhang, Weihe, Luo, Shengjun, Fang, Chen, Qingshou, Hu, Hanwei, Jia, Xueshun, Zhai, Hongbin
Format: Article
Language:English
Subjects:
Artemisia absinthium - chemistry
Biological and medical sciences
Chemistry
Digestive system
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Medical sciences
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Sesquiterpenes, Guaiane - chemical synthesis
Stereoisomerism
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Summary:(+)-Absinthin, a structurally unique triterpene, has been efficiently constructed in nine reaction steps and in 18.6% overall yield from O-acetylisophotosantonic lactone. The synthesis features Mitsunobu arylselenylation, oxidative elimination of allylic arylselenides, biomimetic dimerization via regio- and stereospecific Diels−Alder reaction, and a four-step stereochemical inversion of a highly sterically congested tertiary alcohol. This approach has not only tackled the formidable synthetic challenges in assembling structurally complex (+)-absinthin but also paved an efficient synthetic route to a series of medicinally attractive absinthin analogues.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0439219