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 |
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ページ(範囲) | 1059-1070 |
ページ数 | 12 |
ジャーナル | Tetrahedron |
巻 | 74 |
号 | 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