Total synthesis of absinthin

W Zhang, S Luo, F Fang, Q Chen, H Hu…

Index: Zhang, Weihe; Luo, Shengjun; Fang, Fang; Chen, Qingshou; Hu, Hanwei; Jia, Xueshun; Zhai, Hongbin Journal of the American Chemical Society, 2005 , vol. 127, # 1 p. 18 - 19

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Citation Number: 60

Abstract

(+)-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 ...