Bioinspired total synthesis of boneratamides A-C

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

*この研究の対応する著者

研究成果: Article査読

抄録

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.

本文言語English
ページ(範囲)8236-8242
ページ数7
ジャーナルOrganic and Biomolecular Chemistry
20
42
DOI
出版ステータスPublished - 2022 9月 24

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

フィンガープリント

「Bioinspired total synthesis of boneratamides A-C」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル