二量体型リコポジウムアルカロイド・コンプラナジンAおよびBの全合成

• 趙 楽

• 權 垠相

• 竹本 佳司

• 平間 正博

• 塚野 千尋

  京都大学大学院薬学研究科

書誌事項

タイトル別名

• Total Syntheses of Dimmeric Lycopodium Alkaloid, Complanadines A and B
• ニリョウ タイケイ リコポジウムアルカロイド ・ コンプラナジン A オヨビ B ノ ゼン ゴウセイ

抄録

Our total syntheses of lycopodium alkaloid lycodine (1), and its unsymmetric dimmer complanadines A (3) and B (4) were described. The bicyclo[3.3.1]nonane core structure of lycodine was constructed by regioselective Diels-Alder and intramolecular Mizoroki-Heck reactions. A late-stage coupling reaction of the lycodine units, pyridine N-oxide (+)-17 and aryl bromide (+)-16, through C-H arylation at the C1 position of (+)-17 provided the unsymmetric dimer structure. This strategy significantly simplified the construction of the dimeric architecture and functionalization. Total syntheses of complanadines A (3) and B (4) were achieved by adjusting the oxidation level of the bipyridine mono-N-oxide (+)-18. The diverse utility of this common intermediate (+)-18 suggests a possible biosynthetic pathway of complanadines in nature. Both enantiomers of lycodine (1) and complanadines A (3) and B (4) were prepared in sufficient quantities. The effect on neuron differentiation of PC-12 cells with human astrocytoma cells culture medium was evaluated.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 77 (2), 135-144, 2019-02-01

  公益社団法人 有機合成化学協会

キーワード

• lycopodium alkaloid
• total synthesis
• dimmerization
• Diels-Alder reaction
• Mizoroki-Heck reaction
• C-H activation
• divergent synthesis
• biosynthetic hypothesis
• neuron differentiation

詳細情報

• CRID: 1390282763098771712
• NII論文ID: 130007596426
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.77.135
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 029510727
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029510727
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/77/2/77_135/_pdf
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可