Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

Teruhiko Ishikawa, Hirokazu Ishii, Kazuo Shimizu, Hiroe Nakao, Jin Urano, Takayuki Kudo, Seiki Saito

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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.

Original languageEnglish
Pages (from-to)8133-8135
Number of pages3
JournalJournal of Organic Chemistry
Volume69
Issue number23
DOIs
Publication statusPublished - Nov 12 2004

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ishikawa, T., Ishii, H., Shimizu, K., Nakao, H., Urano, J., Kudo, T., & Saito, S. (2004). Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid. Journal of Organic Chemistry, 69(23), 8133-8135. https://doi.org/10.1021/jo048738c