title: Synthesis of chiral hexasubstituted cyclohexanediol, a key intermediate for the synthesis of verticillol, from (+)-dihydrocarvone; attempted cyclization to 12-membered carbocycle in verticillol using RCM reaction.
abstract: A cyclohexane derivative with three chiral centers, a key intermediate for the synthesis of a diterpene verticillol, was prepared starting from (+)-dihydrocarvone. A further challenge to cyclize to a 12-membered carbocycle was attempted, although the products were dimeric derivatives presumably due to an undesirable conformation of the substrate.
authors.forename: Katsuyuki
authors.initials: K
authors.lastname: Nakashima
authors.forename: Yuzuru
authors.initials: Y
authors.lastname: Kondo
authors.forename: Kosei
authors.initials: K
authors.lastname: Yoshimasu
authors.forename: Masakazu
authors.initials: M
authors.lastname: Sono
authors.forename: Motoo
authors.initials: M
authors.lastname: Tori
mesh_terms: D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D003510:Cyclohexanes / Q000138:chemical synthesis*; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry*
chemical_list: D000081005:Cyclohexane Monoterpenes; D003510:Cyclohexanes; D003511:Cyclohexanols; D047028:Macrocyclic Compounds; D039821:Monoterpenes; C556859:dihydrocarvone