title: Stereospecific Construction of Contiguous Quaternary All-Carbon Centers by Oxidative Ring Contraction.
abstract: Oxidative ring contraction of cyclic α-formyl ketones was facilitated by the action of H2O2under operationally simple and environmentally benign reaction conditions. The process was highly regioselective and enables stereospecific construction of contiguous quaternary all-carbon centers from stereodefined all-substituted all-cyclic ketones. The asymmetric syntheses of (+)-cuparene and (+)-tochuinyl acetate were also successively achieved by taking advantage of this novel protocol.
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, 712100, Shaanxi, China.|Shanghai University, Shanghai, 200444, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Yu
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, 712100, Shaanxi, China.
authors.forename: Jiadong
authors.initials: J
authors.lastname: Hu
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
authors.forename: Zhigao
authors.initials: Z
authors.lastname: Shen
authors.affiliation: Shanghai University, Shanghai, 200444, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, 712100, Shaanxi, China.
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, 712100, Shaanxi, China.
authors.forename: Weiqing
authors.initials: W
authors.lastname: Xie
keywords: natural products; oxidation; rearrangements; ring contraction; total synthesis