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

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery

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    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