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

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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Terpenes
Biosynthesis
Biological Products
Cyanides
Formaldehyde
Oxidation

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Bioinspired Synthesis of the Central Core of Halichonadin H : The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products. / Ichikawa, Yoshiyasu; Yamasaki, Toshiki; Nakanishi, Keisuke; Udagawa, Yutaro; Hosokawa, Seijiro; Masuda, Toshiya.

In: Synthesis (Germany), Vol. 51, No. 11, 01.01.2019, p. 2305-2310.

Research output: Contribution to journalArticle

Ichikawa, Yoshiyasu ; Yamasaki, Toshiki ; Nakanishi, Keisuke ; Udagawa, Yutaro ; Hosokawa, Seijiro ; Masuda, Toshiya. / Bioinspired Synthesis of the Central Core of Halichonadin H : The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products. In: Synthesis (Germany). 2019 ; Vol. 51, No. 11. pp. 2305-2310.
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