Ring-opening cyclization of spirocyclopropanes using sulfoxonium ylides

Yuta Onuki, Hisanori Nambu*, 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

12 被引用数 (Scopus)

抄録

Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes using dimethylsulfoxonium methylide proceeded regioselectively to produce 2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-ones in good to high yields. The reactions of cycloheptane- and cyclopentane-1,3-dione-2-spirocyclopropanes could construct [7.6]- and [5.6]-fused ring systems. This reaction was also carried out using sulfoxonium ethylide, butylide, and benzylide, resulting in the formation of the corresponding 2,3-trans-disubstituted products in good to high yields, and it was shown that the dimethyl group can act as a dummy substituent. It was found that the 2- and 3-phenyhexahydrobenzopyran-5-ones can be readily converted into 5-hydroxyflavan and 5-hydroxy-isoflavan, respectively.

本文言語英語
ページ(範囲)479-486
ページ数8
ジャーナルChemical and Pharmaceutical Bulletin
68
5
DOI
出版ステータス出版済み - 2020

ASJC Scopus 主題領域

  • 化学一般
  • 創薬

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