Total Synthesis of (−)-Histrionicotoxin through a Stereoselective Radical Translocation–Cyclization Reaction

Manabu Sato, Hiroki Azuma, Akihiro Daigaku, Sota Sato, Kiyosei Takasu, Kentaro Okano, Hidetoshi Tokuyama

研究成果: Article査読

36 被引用数 (Scopus)

抄録

Stereoselective total syntheses of (−)-histrionicotoxin and (−)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation–cyclization reaction involving a chiral cyclic acetal; the use of tris(trimethylsilyl)silane was crucial for the high diastereoselectivity. The cyclization product was converted into (−)-histrionicotoxin 235A through a one-pot partial-reduction–allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (−)-histrionicotoxin.

本文言語English
ページ(範囲)1087-1091
ページ数5
ジャーナルAngewandte Chemie - International Edition
56
4
DOI
出版ステータスPublished - 2017 1月 19

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)

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