Development of TfOH-Catalyzed Spirocyclization by Intramolecular Friedel-Crafts-type 1,4-Addition: Application to the Total Synthesis of the Unusual Proaporphine Alkaloid (±)-Misrametine

Keisuke Yoshida, Arisa Hidaka, Yuri Fukami, Yuta Fujino, Yuri Imaizumi, Ken ichi Takao, Shinji Kitagaki

研究成果: Article査読

抄録

An effective method was developed for TfOH-catalyzed construction of spiroindanes and spirotetralines containing an all-carbon quaternary stereocenter. Intramolecular Friedel-Crafts-type 1,4-addition of the substrates which were di- or trimethoxybenzene and 2-cyclohexenone linked by an alkyl chain proceeded smoothly in the presence of 30 mol % of TfOH. A variety of spiroindanes and spirotetralines were obtained with moderate to excellent yield by this method. The reaction was successfully applied in the first total synthesis of the unusual proaporphine alkaloid (±)-misrametine, which included the gram-scale spirocyclization and selective O-demethylation used KCN in DMSO condition as key steps.

本文言語English
論文番号e202202188
ジャーナルChemistry - A European Journal
28
60
DOI
出版ステータスPublished - 2022 10月 26

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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「Development of TfOH-Catalyzed Spirocyclization by Intramolecular Friedel-Crafts-type 1,4-Addition: Application to the Total Synthesis of the Unusual Proaporphine Alkaloid (±)-Misrametine」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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