Recent Advances for Synthesis of Scyphostatin and Utilization of Oxabicyclo[2.2.1]Heptene Toward Ethyl Shikimate

Kazuaki Kuwata; Yasunobu Yamashita; Kengo Hanaya; Takeshi Sugai; Tohru Mizushima; Mitsuru Shoji

doi:10.1016/B978-0-444-63603-4.00012-7

Recent Advances for Synthesis of Scyphostatin and Utilization of Oxabicyclo[2.2.1]Heptene Toward Ethyl Shikimate

Kazuaki Kuwata, Yasunobu Yamashita, Kengo Hanaya, Takeshi Sugai, Tohru Mizushima, Mitsuru Shoji

School of Pharmaceutical Sciences

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Abstract

Diels-Alder reaction of furan and acrylic chloride or acrylic acid provides oxabicyclo[2.2.1]heptenes with three chiral centers. We have prepared epoxycyclohexenol (+)-3 and acetate (-)-4 with high enantiomeric excess from Diels-Alder adduct 1 via lipase-mediated kinetic resolution. Recently, we synthesized scyphostatin hydrophilic core 52 and ethyl shikimate (10) via optically active alcohols 3 and 8, respectively. In this review, we are going to describe several syntheses of scyphostatin (6) and synthetic utility of polyoxygenated carbacycles such as 3, 4, 8, and 9 toward natural products.

Original language	English
Title of host publication	Studies in Natural Products Chemistry, 2016
Publisher	Elsevier
Pages	387-403
Number of pages	17
ISBN (Print)	9780444636034
DOIs	https://doi.org/10.1016/B978-0-444-63603-4.00012-7
Publication status	Published - 2016

Publication series

Name	Studies in Natural Products Chemistry
Volume	47
ISSN (Print)	1572-5995

Keywords

diastereoselective reaction
ethyl shikimate
kinetic resolution
oxabicycloheptene
scyphostatin

ASJC Scopus subject areas

Drug Discovery
Organic Chemistry

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10.1016/B978-0-444-63603-4.00012-7

Cite this

Kuwata, K., Yamashita, Y., Hanaya, K., Sugai, T., Mizushima, T., & Shoji, M. (2016). Recent Advances for Synthesis of Scyphostatin and Utilization of Oxabicyclo[2.2.1]Heptene Toward Ethyl Shikimate. In Studies in Natural Products Chemistry, 2016 (pp. 387-403). (Studies in Natural Products Chemistry; Vol. 47). Elsevier. https://doi.org/10.1016/B978-0-444-63603-4.00012-7

Recent Advances for Synthesis of Scyphostatin and Utilization of Oxabicyclo[2.2.1]Heptene Toward Ethyl Shikimate. / Kuwata, Kazuaki; Yamashita, Yasunobu; Hanaya, Kengo et al.
Studies in Natural Products Chemistry, 2016. Elsevier, 2016. p. 387-403 (Studies in Natural Products Chemistry; Vol. 47).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

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abstract = "Diels-Alder reaction of furan and acrylic chloride or acrylic acid provides oxabicyclo[2.2.1]heptenes with three chiral centers. We have prepared epoxycyclohexenol (+)-3 and acetate (-)-4 with high enantiomeric excess from Diels-Alder adduct 1 via lipase-mediated kinetic resolution. Recently, we synthesized scyphostatin hydrophilic core 52 and ethyl shikimate (10) via optically active alcohols 3 and 8, respectively. In this review, we are going to describe several syntheses of scyphostatin (6) and synthetic utility of polyoxygenated carbacycles such as 3, 4, 8, and 9 toward natural products.",

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AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Mizushima, Tohru

AU - Shoji, Mitsuru

PY - 2016

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AB - Diels-Alder reaction of furan and acrylic chloride or acrylic acid provides oxabicyclo[2.2.1]heptenes with three chiral centers. We have prepared epoxycyclohexenol (+)-3 and acetate (-)-4 with high enantiomeric excess from Diels-Alder adduct 1 via lipase-mediated kinetic resolution. Recently, we synthesized scyphostatin hydrophilic core 52 and ethyl shikimate (10) via optically active alcohols 3 and 8, respectively. In this review, we are going to describe several syntheses of scyphostatin (6) and synthetic utility of polyoxygenated carbacycles such as 3, 4, 8, and 9 toward natural products.

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KW - oxabicycloheptene

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Recent Advances for Synthesis of Scyphostatin and Utilization of Oxabicyclo[2.2.1]Heptene Toward Ethyl Shikimate

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