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 |
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ページ(範囲) | 8236-8242 |
ページ数 | 7 |
ジャーナル | Organic and Biomolecular Chemistry |
巻 | 20 |
号 | 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