Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecular Heck reaction.
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).
Node
Manabu
M
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
Ozeki
Minoru
M
Planas
Loïc
L
Nakano
Masashi
M
Takita
Hirofumi
H
Mori
Daisuke
D
Tamatani
Shinji
S
Kajimoto
Tetsuya
T
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
D045784:Abietanes; D004224:Diterpenes; D008024:Ligands; C516090:dichroanal B; C516091:dichroanone; C516088:taiwaniaquinone H