title: Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecular Heck reaction.
abstract: The synthesis of the abeo-abietane-type diterpenoids, i.e., (-)-dichroanal B, (-)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).
authors.affiliation: Department of Pharmaceutical Manufacturing Chemistry, 21st COE Program, Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan. node@mb.kyoto-phu.ac.jp
authors.forename: Manabu
authors.initials: M
authors.lastname: Node
authors.forename: Minoru
authors.initials: M
authors.lastname: Ozeki
authors.forename: Loïc
authors.initials: L
authors.lastname: Planas
authors.forename: Masashi
authors.initials: M
authors.lastname: Nakano
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Takita
authors.forename: Daisuke
authors.initials: D
authors.lastname: Mori
authors.forename: Shinji
authors.initials: S
authors.lastname: Tamatani
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kajimoto
mesh_terms: D045784:Abietanes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D045784:Abietanes; D004224:Diterpenes; D008024:Ligands; C516090:dichroanal B; C516091:dichroanone; C516088:taiwaniaquinone H