title: Asymmetric Total Synthesis of (-)-Kravanhin B.
abstract: The first asymmetric total synthesis of kravanhin B has been accomplished with a linear reaction sequence of 13 steps starting from (R)-(-)-carvone. The synthesis features an intramolecular aldol cyclization to construct the desired cis-fused decalin skeleton and an acid-catalyzed dehydration and olefin isomerization to install the γ-butenolide ring.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
authors.forename: Zhuliang
authors.initials: Z
authors.lastname: Zhong
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
authors.forename: Donghui
authors.initials: D
authors.lastname: Ma
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
authors.forename: Gaoyuan
authors.initials: G
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
authors.forename: Huilin
authors.initials: H
authors.lastname: Li
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
authors.forename: Dengyu
authors.initials: D
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
authors.forename: Xingang
authors.initials: X
authors.lastname: Xie
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China. shexg@lzu.edu.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, P. R. China. shexg@lzu.edu.cn.
authors.forename: Xuegong
authors.initials: X
authors.lastname: She
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D039821:Monoterpenes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000081005:Cyclohexane Monoterpenes; D004224:Diterpenes; D039821:Monoterpenes; C580650:kravanhin B; C006923:carvone; C116609:3-hydroxybutanal; C004511:butenolide; D015107:4-Butyrolactone
keywords: aldol reaction; asymmetric synthesis; total synthesis; trans-anti-cis