Divergent synthesis of (+)-tanikolide and its analogues employing stereoselective rhodium(II)-catalyzed reaction

Hikari Jinnouchi, Hisanori Nambu, Tomoya Fujiwara, Takayuki Yakura*

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

14 被引用数 (Scopus)

抄録

In this study, we described the divergent synthesis of (+)-tanikolide and its analogues, such as (4S)- and (4R)-hydroxytanikolides, and nortanikolide, employing a stereoselective dirhodium(II)-catalyzed reaction to construct the quaternary chiral center of tanokolides. The key steps involve (a) a dirhodium(II)-catalyzed oxonium ylide formation–[2,3]-sigmatropic rearrangement, (b) an N-heterocyclic carbene-catalyzed ring-expansion lactonization of tetrahydrofurfural, or (c) an oxidative cleavage of tetrahydrofuran-5-methanol to γ-lactone using a 2-iodobenzamide catalyst. This route would provide high flexibility for analogue synthesis because the long side chain can be introduced at a later stage in the synthesis.

本文言語英語
ページ(範囲)1059-1070
ページ数12
ジャーナルTetrahedron
74
10
DOI
出版ステータス出版済み - 2018/03/08

ASJC Scopus 主題領域

  • 生化学
  • 創薬
  • 有機化学

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