Bioinspired total synthesis of bolivianine: A diels-alder/intramolecular hetero-Diels-Alder cascade approach

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[1] Yuan, Changchun
[2] Du, Biao
[3] Yang, Li
[4] 1,Liu, Bo
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Liu, B. (chembliu@scu.edu.cn) | 1600年 / American Chemical Society卷 / 135期
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We report the first total synthesis of bolivanine in a 14-step pathway involving the synthesis of onoseriolide. Our synthesis features a palladium-catalyzed intramolecular cyclopropanation involving an allylic metal carbene and a Diels-Alder/intramolecular hetero-Diels-Alder cascade; allowing the single-step assembly of a tricyclic system with proper configuration. The synthetic efforts validate our modified biogenetic hypothesis and allow us to confirm the absolute configuration of bolivianine. © 2013 American Chemical Society;
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