Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

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

Research output: Contribution to journalArticle

19 Citations (Scopus)

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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9-O-methanoprostaglandin I
Ascorbic Acid

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

Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid. / Ishikawa, Teruhiko; Ishii, Hirokazu; Shimizu, Kazuo; Nakao, Hiroe; Urano, Jin; Kudo, Takayuki; Saito, Seiki.

In: Journal of Organic Chemistry, Vol. 69, No. 23, 12.11.2004, p. 8133-8135.

Research output: Contribution to journalArticle

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, vol. 69, no. 23, pp. 8133-8135. https://doi.org/10.1021/jo048738c
Ishikawa, Teruhiko ; Ishii, Hirokazu ; Shimizu, Kazuo ; Nakao, Hiroe ; Urano, Jin ; Kudo, Takayuki ; Saito, Seiki. / Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 23. pp. 8133-8135.
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