Stereoselective total synthesis of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone based on a Claisen rearrangement |
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Authors: | Atsuo Nakazaki |
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Institution: | Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan |
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Abstract: | The stereoselective total syntheses of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone were accomplished based on a Claisen rearrangement in an alkenyl bicyclic dihydropyran system. The most striking feature of this approach is that the Claisen rearrangement of bicyclic dihydropyran proceeds stereoselectively to provide a multi-functionalized spiro4.5]decane, which is an efficient precursor for the synthesis of the vetivane sesquiterpenes. |
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Keywords: | Vetivane sesquiterpene Spiro[4 5]decane Claisen rearrangement |
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