Total Synthesis of the Proposed Structure of Turkiyenine

Hisataka Kobayashi, Yusuke Sasano, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

研究成果: Article査読

12 被引用数 (Scopus)

抄録

The secondary metabolite, turkiyenine, is a probable bioactive component of the medicinal plant, Hypecoum procumbens L. Structurally, it is an isoquinoline-derived alkaloid composed of dihydrobenzofuran and 3-benzazepine-1-one moieties arranged in a unique spirocyclic structure. Yet despite the intriguing structure and medicinal relevance of benzofuran and benzazepine motifs, neither a synthetic study nor a biological evaluation of turkiyenine have been reported to date. Herein we communicate the first total synthesis of the proposed structure of turkiyenine, and on the basis of X-ray crystallography show that the proposed structure is incorrect. The key steps of our synthesis include an aza-spiro annulation onto a benzofuran using a rhodium-nitrenoid to construct a 3-alkyl-3-amino-2,3-dihydrobenzofuran, an acyl-alkylation of an aryne onto a β-ketolactam to form a 3-benzazepine-1-one, and chemoselective reduction of an amide in the presence of a ketone.

本文言語English
ページ(範囲)270-273
ページ数4
ジャーナルEuropean Journal of Organic Chemistry
2016
2
DOI
出版ステータスPublished - 2016 1

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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