Synthesis of pyrrolophenanthridine alkaloids based on C(sp³)[BOND]H and C(sp²)[BOND]H functionalization reactions.

• 塚野, 千尋

• Muto, Nobusuke

• Enkhtaivan, Iderbat

• 竹本, 佳司

抄録

Assoanine, pratosine, hippadine, and dehydroanhydrolycorine belong to the pyrrolophenanthridine family of alkaloids, which are isolated from plants of the Amaryllidaceae species. Structurally, these alkaloids are characterized by a tetracyclic skeleton that contains a biaryl moiety and an indole core, and compounds belonging to this class have received considerable interest from researchers in a number of fields because of their biological properties and the challenges associated with their synthesis. Herein, a strategy for the total synthesis of these alkaloids by using C-H activation chemistry is described. The tetracyclic skeleton was constructed in a stepwise manner by C(sp(3))[BOND]H functionalization followed by a Catellani reaction, including C(sp(2))[BOND]H functionalization. A one-pot reaction involving both C(sp(3))[BOND]H and C(sp(2))[BOND]H functionalization was also attempted. This newly developed strategy is suitable for the facile preparation of various analogues because it uses simple starting materials and does not require protecting groups.

Article first published online: 14 JUL 2014

収録刊行物

• Chemistry, an Asian journal

  Chemistry, an Asian journal 9 (9), 2628-2634, 2014-09

  Wiley

キーワード

• alkaloids
• C[BOND]H activation
• natural products
• synthesis design
• total synthesis
• Alkaloids/chemical synthesis
• Alkaloids/chemistry
• Carbon/chemistry
• Hydrogen/chemistry
• Molecular Structure
• Phenanthridines/chemical synthesis
• Phenanthridines/chemistry
• Pyrroles/chemical synthesis
• Pyrroles/chemistry

詳細情報

• CRID: 1050282810790299776
• NII論文ID: 120005649315
• NII書誌ID: AA12151701
• ISSN: 18614728
• ISSN: 1861471X
• HANDLE: 2433/199674
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles