Total Synthesis of Avenaol, non-Canonical Strigolactone

• Tsukano Chihiro

  Graduate School of Pharmaceutical Sciences, Kyoto University

Bibliographic Information

Other Title

• 非典型ストリゴラクトン・アベナオールの全合成
• ヒテンケイ ストリゴラクトン ・ アベナオール ノ ゼン ゴウセイ

Abstract

The first total synthesis of avenaol, which is the first reported natural C₂₀ germination stimulant structurally related to strigolactones, was achieved using a new robust strategy involving all-cis-substituted cyclopropane formation via an alkylidencyclopropane. The keys to success for the total synthesis were (i) Rh-catalyzed intramolecular cyclopropanation of an allene, (ii) Ir-catalyzed stereoselective double-bond isomerization, and (iii) regioselective oxidation of tetrahydropyran. This strategy effectively avoids cyclopropane ring opening and undesired formation of a cage structure.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 76 (5), 486-489, 2018-05-01

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• avenaol
• strigolactone
• <i>all</i>-<i>cis</i>-cyclopropane
• total synthesis
• alkylidencyclopropane

Details

• CRID: 1390282680315934336
• NII Article ID: 130006733910
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.76.486
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 029057659
• Web Site: http://id.ndl.go.jp/bib/029057659
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029057659
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/76/5/76_486/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed