全シス置換シクロプロパン構築法の確立とAvenaolの全合成

• 安井 基博

  京都大学大学院薬学研究科

書誌事項

タイトル別名

• Construction of All-<i>cis</i>-substituted Cyclopropane and Total Synthesis of Avenaol
• Review for award 全シス置換シクロプロパン構築法の確立とAvenaolの全合成
• Review for award ゼン シス チカン シクロプロパン コウチクホウ ノ カクリツ ト Avenaol ノ ゼン ゴウセイ

抄録

The first total synthesis of avenaol was achieved using a new robust strategy involving all-cis-substituted cyclopropane formation via an alkylidene cyclopropane. The keys to success for the total synthesis were (i) Rh-catalyzed intramolecular cyclopropanation of an allene; (ii) Ir-catalyzed stereoselective double-bond isomerization to form an all-cis cyclopropane; and (iii) differentiation of two hydroxymethyl groups via regioselective cyclization and oxidation of tetrahydropyran based on the reactivity of cyclopropyl group. This strategy effectively avoids cyclopropane ring opening and undesired formation of a cage structure. Additionally, the proposed structure of avenaol, especially unique all-cis-substituted cyclopropane was confirmed correct by this total synthesis.

収録刊行物

• 薬学雑誌

  薬学雑誌 139 (10), 1259-1265, 2019-10-01

  公益社団法人 日本薬学会

キーワード

• avenaol
• total synthesis
• cyclopropane
• isomerization
• strigolactone
• Crabtree's catalyst

詳細情報

• CRID: 1390282752340243200
• NII論文ID: 130007721911
• NII書誌ID: AN00284903
• DOI: 10.1248/yakushi.19-00130
• ISSN: 13475231
• ISSN: 00316903
• NDL書誌ID: 030016737
• PubMed: 31582609
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030016737
• Web Site: https://www.jstage.jst.go.jp/article/yakushi/139/10/139_19-00130/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2020191725
• 本文言語コード: ja
• データソース種別:
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  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
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