title: Enantioselective synthesis of (+)-brevipolide H.
abstract: The enantioselective synthesis of natural brevipolide H is reported for the first time. By way of Sharpless epoxidation of penta-1,4-dien-3-ol, both enantiomerically pure epoxides were converted to the corresponding olefins for cross metathesis. Subsequent transformations, including epoxide ring opening, esterifications, cyclopropanation, oxidation and ring-closing metathesis, provided the target molecule. This synthesis successfully addresses previous shortcomings in preparing brevipolides.
authors.affiliation: Department of Chemistry, National Central University, No. 300 Jhong-Da Rd., Jhong-li, Taoyuan 32001, Taiwan. drhou@ncu.edu.tw.
authors.forename: Ching-Nung
authors.initials: CN
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Central University, No. 300 Jhong-Da Rd., Jhong-li, Taoyuan 32001, Taiwan. drhou@ncu.edu.tw.
authors.forename: Duen-Ren
authors.initials: DR
authors.lastname: Hou
mesh_terms: D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D004951:Esterification; D031331:Hyptis / Q000737:chemistry; D010084:Oxidation-Reduction; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D004852:Epoxy Compounds; D011753:Pyrones; C000592380:brevipolide H; C030797:cyclopropane