A general strategy for synthesis of both (6Z)- and (6E)-cladiellin diterpenes: total syntheses of (-)-cladiella-6,11-dien-3-ol, (+)-polyanthellin A, (-)-cladiell-11-ene-3,6,7-triol, and (-)-deacetoxyalcyonin acetate.
The first total synthesis of an (E)-cladiellin diterpene, (-)-cladiella-6,11-diene-3-ol (1), was accomplished featuring an intramolecular amide enolate alkylation-intramolecular Diels-Alder strategy. In addition, a highly stereo-, regio-, and chemoselective synthetic strategy for other members of the cladiellin diterpenes such as (+)-polyanthellin A (2), (-)-cladiell-11-ene-3,6,7-triol (3), and (-)-deacetoxyalcyonin acetate (4) was developed utilizing the synthetic (E)-cladiellin 1 as a common intermediate by taking advantage of the unique chemical properties of its C(6)-(E)-oxatricyclic skeleton.
Kim
Hyoungsu
H
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, San 56-1, Shinrim-Dong, Kwanak-Ku, Seoul 151-742, Korea.
Lee
Hyunjoo
H
Kim
Jayoung
J
Kim
Sanghee
S
Kim
Deukjoon
D
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D008956:Models, Chemical; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis*
C439393:6-acetoxycladiell-7(16),11-dien-3-ol; D001952:Bridged-Ring Compounds; D004224:Diterpenes; D005663:Furans; D013256:Steroids; C430551:cladiell-11-ene-3,6,7-triol; C506145:cladiellin A; C476739:polyanthellin A