Bioinspired total synthesis of boneratamides A-C

Kaito Ooka, Keisuke Nakanishi, Yutaro Udagawa, Yoshiyasu Ichikawa*, Seijiro Hosokawa

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

We disclose the first synthesis of the marine natural product, (+)-boneratamide A, whose structure is composed of a terpene unit linked via an amide bond to a pyroglutamic acid moiety. The key step in this route is a bioinspired Ugi reaction of (+)-axisonitrile-3 with acetone as the carbonyl component and l-glutamic acid. This reaction brings about a remarkably efficient, one-pot assembly of reaction components concomitant with γ-lactam ring formation to produce (+)-boneratamide A in 70% yield. (+)-Boneratamide B and (-)-boneratamide C methyl esters were also synthesized using a similar bioinspired strategy, and the relative stereochemistries at the stereogenic centers in these substances were elucidated using X-ray analysis.

Original languageEnglish
Pages (from-to)8236-8242
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume20
Issue number42
DOIs
Publication statusPublished - 2022 Sep 24

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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