Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

Teruhiko Ishikawa; Hirokazu Ishii; Kazuo Shimizu; Hiroe Nakao; Jin Urano; Takayuki Kudoh; Seiki Saito

doi:10.1021/jo048738c

Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

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

Research output: Contribution to journal › Article › peer-review

21 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 language	English
Pages (from-to)	8133-8135
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	69
Issue number	23
DOIs	https://doi.org/10.1021/jo048738c
Publication status	Published - Nov 12 2004

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo048738c

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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.",

author = "Teruhiko Ishikawa and Hirokazu Ishii and Kazuo Shimizu and Hiroe Nakao and Jin Urano and Takayuki Kudoh and Seiki Saito",

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T1 - Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

AU - Ishikawa, Teruhiko

AU - Ishii, Hirokazu

AU - Shimizu, Kazuo

AU - Nakao, Hiroe

AU - Urano, Jin

AU - Kudoh, Takayuki

AU - Saito, Seiki

PY - 2004/11/12

Y1 - 2004/11/12

N2 - 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.

AB - 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.

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JO - Journal of Organic Chemistry

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ER -

Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

Abstract

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