Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products

Yoshiyasu Ichikawa, Toshiki Yamasaki, Keisuke Nakanishi, Yutaro Udagawa, Seijiro Hosokawa, Toshiya Masuda

研究成果: Article

1 引用 (Scopus)

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A pathway is proposed for the biosynthesis of the unique homodimeric terpene, halichonadin H. The proposed biosynthetic pathway involves two key Passerini reactions of eudesmane-type terpene isocyanides. The Passerini reaction of a model terpene isocyanide and formaldehyde afforded an α-hydroxy acetamide, which was further subjected to oxidation and a second Passerini reaction. This reaction sequence furnished an α-hydroxy malonamide connected with two identical terpene units which is the identical structural motif found in halichonadin H.

元の言語English
ページ(範囲)2305-2310
ページ数6
ジャーナルSynthesis (Germany)
51
発行部数11
DOI
出版物ステータスPublished - 2019 1 1

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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