Asymmetric synthesis of the oxygenated polycyclic system of (+)-harringtonolide |
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Authors: | Abdelkafi Hajer Herson Patrick Nay Bastien |
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Institution: | Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro-organismes (UMR 7245 CNRS-MNHN), 57 rue Cuvier (CP 54), 75005 Paris, France. |
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Abstract: | A straightforward asymmetric synthesis of the cage oxygenated structure of (+)-harringtonolide has been accomplished for the first time. The key steps involved (i) a templated stereoselective IMDA reaction to build a highly functionalized cyclohexene ring D, (ii) functionalization of the cycloadduct, (iii) ring-closing metathesis providing the five-membered ring C, and finally (iv) a challenging one-step cascade cyclization of an epoxy-alcohol toward the target structure, whose mechanism was investigated. |
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