Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid.
作者信息
Ishikawa Teruhiko, Ishii Hirokazu, Shimizu Kazuo, Nakao Hiroe, Urano Jin, Kudo Takayuki, Saito Seiki
机构信息
School of Education, and Department of Bioscience and Biotechnology, School of Engineering, Okayama University, Tsushima, Okayama, Japan.
出版信息
J Org Chem. 2004 Nov 12;69(23):8133-5. doi: 10.1021/jo048738c.
PMID:15527306
Abstract
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.
摘要
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