| Autor: |
Kaito Ooka, Keisuke Nakanishi, Yutaro Udagawa, Yoshiyasu Ichikawa, Seijiro Hosokawa |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Organicbiomolecular chemistry. 20(42) |
| ISSN: |
1477-0539 |
| Popis: |
We disclose the first synthesis of the marine natural product, (+)-boneratamide A, whose structure is composed of a terpene unit linkedivia/ian 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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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