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

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2305-2310
Number of pages6
JournalSynthesis (Germany)
Volume51
Issue number11
DOIs
Publication statusPublished - 2019 Jan 1

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Keywords

  • biosynthesis
  • isocyanides
  • marine natural products
  • Passerini reaction
  • terpenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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