title: Convergent Route to ent-Kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α,6α-Diacetoxy-ent-kaura-9(11),16-dien-12,15-dione.
abstract: The Hoppe's homoaldol reaction of a cyclo-hexenyl carbamate with an aldehyde followed by an unprecedented BF3·OEt2mediated intramolecular Mukaiyama-Michael-type reaction affords the tetracyclic core structure of ent-kaurane diterpenoids. The usage of this convergent approach for assembling these natural products is demonstrated by the first asymmetric total syntheses of two highly oxidized ent-kaurane diterpenoids: Lungshengenin D and 1α,6α-diacetoxy-ent-kaura-9(11),16-dien-12,15-dione.
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Xiangbo
authors.initials: X
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Wu
authors.initials: W
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Junjie
authors.initials: J
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Dawei
authors.identifier: 0000-0002-1721-7551
authors.initials: D
authors.lastname: Ma
mesh_terms: D045786:Diterpenes, Kaurane / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C000627254:1alpha,6alpha-Diacetoxy-ent-kaura-9(11),16-dien-12,15-dione; D045786:Diterpenes, Kaurane; C000627255:lungshengenin D