title: A protecting group-free synthesis of (-)-hortonones A-C from the Inhoffen-Lythgoe diol.
abstract: A synthesis of hortonones A-C has been accomplished from vitamin D2via the Inhoffen-Lythgoe diol without the use of protective groups. Key steps in the syntheses include a TMS-diazomethane mediated regioselective homologation of the cyclohexanone ring to a cycloheptanone moiety and a sodium naphthalenide-mediated allylic alcohol transposition. It has been found that the absolute configuration of the natural hortonones is opposite that of the synthetic material prepared from vitamin D2.
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, CA 91330, USA. thomas.minehan@csun.edu.
authors.forename: Hovsep
authors.initials: H
authors.lastname: Stambulyan
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, CA 91330, USA. thomas.minehan@csun.edu.
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry; D003978:Diazomethane / Q000138:chemical synthesis / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D004872:Ergocalciferols / Q000138:chemical synthesis / Q000737:chemistry; D029585:Monimiaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000972:Antineoplastic Agents, Phytogenic; D003512:Cyclohexanones; D004224:Diterpenes; D004872:Ergocalciferols; C574878:hortonone A; C574880:hortonone B; C574879:hortonone C; C036468:cyclohexanone; D003978:Diazomethane