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Total Synthesis of Absinthin
journal contribution
posted on 2005-01-12, 00:00 authored by Weihe Zhang, Shengjun Luo, Fang, Qingshou Chen, Hanwei Hu, Xueshun Jia, Hongbin Zhai(+)-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.
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seriestriterpenestericallyabsinthin analoguesoxidative eliminationDielbiomimetic dimerizationapproachmedicinallysynthesis features Mitsunobu arylselenylationallylic arylselenidesfour-step stereochemical inversionregioAbsinthinreaction stepschallengeTotal Synthesisstereospecificacetylisophotosantonic lactone
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