title: Total Synthesis of the Diterpenoid (+)-Harringtonolide.
abstract: Described herein is the first asymmetric total synthesis of (+)-harringtonolide, a natural diterpenoid with an unusual tropone imbedded in a cagelike framework. The key transformations include an intramolecular Diels-Alder reaction and a rhodium-complex-catalyzed intramolecular [3+2] cycloaddition to install the tetracyclic core as well as a highly efficient tropone formation.
authors.affiliation: The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, China.
authors.forename: Hai-Jun
authors.initials: HJ
authors.lastname: Zhang
authors.affiliation: CAS-Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Hu
authors.affiliation: CAS-Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Ma
authors.affiliation: CAS-Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
authors.forename: Ruining
authors.initials: R
authors.lastname: Li
authors.affiliation: The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, China.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, China.
authors.forename: Cheng
authors.initials: C
authors.lastname: Tao
authors.affiliation: The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, China.
authors.forename: Bin
authors.initials: B
authors.lastname: Cheng
authors.affiliation: The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, China.
authors.forename: Yun
authors.initials: Y
authors.lastname: Li
authors.affiliation: Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, Key Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen, 518055, China.
authors.forename: Huifei
authors.initials: H
authors.lastname: Wang
authors.affiliation: The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, China. zhaihb@pkusz.edu.cn.|Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, Key Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen, 518055, China. zhaihb@pkusz.edu.cn.|CAS-Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China. zhaihb@pkusz.edu.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, Tianjin, 300071, China. zhaihb@pkusz.edu.cn.
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhai
keywords: asymmetric synthesis; cycloaddition; natural products; terpenoids; total synthesis