title: Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.
abstract: A total synthesis of the unusual ent-kaurane maoecrystal V is described. The synthesis strategy features a counterintuitive early disconnection of the lactone subunit to a polycyclic enol ether intermediate in order to preserve the central tetrahydrofuran ring until the beginning stages of the synthesis. This strategy enables an application of C-H functionalization at the early phase of the synthesis during the construction of a dihydrobenzofuran intermediate.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93110-9510, United States.
authors.forename: Ping
authors.initials: P
authors.lastname: Lu
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Gu
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D003500:Cyclization; D003603:Cytotoxins / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry; D007783:Lactones / Q000737:chemistry
chemical_list: D001688:Biological Products; D003603:Cytotoxins; D004224:Diterpenes; D005663:Furans; D007783:Lactones; C018674:tetrahydrofuran; C545599:maoecrystal V
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