Total synthesis of natural products using sequential olefin metathesis reactions

Kenichi Takao, Keisuke Yoshida, Kin Ichi Tadano

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Olefin metathesis is established as a remarkably valuable synthetic tool in current organic chemistry. We report here total synthesis of natural products using sequential olefin metathesis reactions. The one - pot ring - opening/cross/ring - closing metathesis (ROM/CM/RCM) reaction has been developed, allowing for the concise construction of the oxygen - bridged 1,3 - cycloocta-diene framework from an oxanorbornene derivative and 1,3-butadiene. The ROM/CM/RCM product was converted into (+)-mycoepoxydiene, (-)-1893A, and (+)-1893B. Furthermore, the ring - opening/ring - closing metathesis (ROM/RCM) of cyclobutenecarboxylate derivatives has been developed as a novel method for access to γ- butenolides. The enantioselective total synthesis of (+)-clavilactone A and (-)-clavilactone B was achieved by the use of this reaction (ROM/RCM).

Original languageEnglish
Pages (from-to)1192-1199
Number of pages8
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume73
Issue number12
Publication statusPublished - 2015

Fingerprint

ROM
Alkenes
Biological Products
Derivatives
Oxygen

Keywords

  • Natural product synthesis
  • Olefin metathesis
  • Ring - closing metathesis
  • Ring - opening/ cross metathesis
  • Ring-opening/ring-closing metathesis
  • Ring-rearrangement metathesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of natural products using sequential olefin metathesis reactions. / Takao, Kenichi; Yoshida, Keisuke; Tadano, Kin Ichi.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 73, No. 12, 2015, p. 1192-1199.

Research output: Contribution to journalArticle

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