Total synthesis of exigurin: The Ugi reaction in a hypothetical biosynthesis of natural products

Seijiro Hosokawa, Keisuke Nakanishi, Yutaro Udagawa, Mitsutoshi Maeda, Seiya Sato, Keiji Nakano, Toshiya Masuda, Yoshiyasu Ichikawa

Research output: Contribution to journalArticle

Abstract

The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.

Original languageEnglish
Pages (from-to)687-693
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number4
DOIs
Publication statusPublished - 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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