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 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.
Zhang
Weihe
W
Laboratory of Modern Synthetic Organic Chemistry and State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China 200032.
Luo
Shengjun
S
Fang
Fang
F
Chen
Qingshou
Q
Hu
Hanwei
H
Jia
Xueshun
X
Zhai
Hongbin
H
D031171:Artemisia absinthium / Q000737:chemistry*; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis*; D013237:Stereoisomerism
D045789:Sesquiterpenes, Guaiane; C499475:absinthin