The first total synthesis of (+/-)-eremopetasidione.
[figure: see text] The total synthesis of racemic eremopetasidione, a norsesquiterpenoid, has been achieved in nine steps and 30% overall yield starting from creosol (5). Diels-Alder reaction of masked o-benzoquinone 6 and ethyl vinyl ketone and Cope rearrangement of 2-silyloxy-1,5-dienone 3 are the key steps.
Hsu
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Department of Chemistry, National Tsing Hua University, Hsinchu-300, Taiwan.
Hsu
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Liao
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D007536:Isomerism; D008516:Medicine, Chinese Traditional; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D018517:Plant Roots; D010946:Plants, Medicinal; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D012717:Sesquiterpenes; C431987:eremopetasidione