title: A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol.
abstract: The first synthetic attempt commencing from an eight-membered ring to approach the [5.3.1] bicyclic core of vinigrol has demonstrated the feasibility of using the conformational bias of the cyclooctane-ring system to realize highly diastereoselective reactions. The synthetic potential of the newly disclosed access to in/out isomerism may stimulate broader interests.
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China. bfsun@sioc.ac.cn.
authors.forename: Xian-Lei
authors.initials: XL
authors.lastname: Wang
authors.forename: Yun-Yu
authors.initials: YY
authors.lastname: Lu
authors.forename: Jie
authors.initials: J
authors.lastname: Wang
authors.forename: Xuan
authors.initials: X
authors.lastname: Wang
authors.forename: He-Quan
authors.initials: HQ
authors.lastname: Yao
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
authors.forename: Bing-Feng
authors.initials: BF
authors.lastname: Sun
mesh_terms: D000478:Alkylation; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D017239:Paclitaxel / Q000737:chemistry; D010165:Palladium; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D004224:Diterpenes; C055112:vinigrol; D010165:Palladium; D017239:Paclitaxel