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

Research output: Chapter in Book/Report/Conference proceedingConference 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 languageEnglish
Title of host publicationStudies in Natural Products Chemistry, 2016
PublisherElsevier
Pages387-403
Number of pages17
Volume47
ISBN (Print)9780444636034
DOIs
Publication statusPublished - 2016

Publication series

NameStudies in Natural Products Chemistry
Volume47
ISSN (Print)15725995

Fingerprint

Cycloaddition Reaction
Biological Products
Lipase
Acrylics
Chlorides
Acetates
Alcohols
Kinetics
scyphostatin
acrylic acid
furan

Keywords

  • diastereoselective reaction
  • ethyl shikimate
  • kinetic resolution
  • oxabicycloheptene
  • scyphostatin

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery

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 (Vol. 47, 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; Sugai, Takeshi; Mizushima, Tohru; Shoji, Mitsuru.

Studies in Natural Products Chemistry, 2016. Vol. 47 Elsevier, 2016. p. 387-403 (Studies in Natural Products Chemistry; Vol. 47).

Research output: Chapter in Book/Report/Conference proceedingConference contribution

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