Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid.
Diastereoselective total synthesis of isocarbacyclin, which features a fused bicyclic key intermediate available from l-ascorbic acid, is described. The key intermediate was prepared in multigram quantities by the Pauson-Khand reaction of l-ascorbic acid-based (R)-4,4-diallyl-2,2-dimethyl-5-(trimethylsilyl)ethynyl-1,3-dioxolane (3), discriminating diastereotopic groups and faces of the geminal allyl substituents.
Ishikawa
Teruhiko
T
School of Education, and Department of Bioscience and Biotechnology, School of Engineering, Okayama University, Tsushima, Okayama, Japan.
Ishii
Hirokazu
H
Shimizu
Kazuo
K
Nakao
Hiroe
H
Urano
Jin
J
Kudo
Takayuki
T
Saito
Seiki
S
D001205:Ascorbic Acid / Q000737:chemistry*; D002384:Catalysis; D011464:Epoprostenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
C041946:9-O-methanoprostaglandin I; D011464:Epoprostenol; D001205:Ascorbic Acid