title: Asymmetric synthesis of the oxygenated polycyclic system of (+)-harringtonolide.
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.
authors.affiliation: 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.
authors.forename: Hajer
authors.initials: H
authors.lastname: Abdelkafi
authors.forename: Patrick
authors.initials: P
authors.lastname: Herson
authors.forename: Bastien
authors.initials: B
authors.lastname: Nay
mesh_terms: D003500:Cyclization; D006248:Harringtonines / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D006248:Harringtonines; C020752:hainanolide