A biomimetic synthesis of the marine thioalkaloids dassonmycins A and B is reported. The synthesis features a chemoselective reduction of a diketopiperazine to form a 2-piperazinone, which undergoes heteroannulation with naphthoquinone to yield dassonmycin A. Dassonmycin A undergoes slow cyclization to form dassonmycin B at physiological pH, supporting a biosynthesis hypothesis that this reaction could occur in the cytosol of the bacterial host species.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c03937 | DOI Listing |
Publication Analysis
Top Keywords
biomimetic synthesis
8
thioalkaloids dassonmycins
8
synthesis marine-derived
4
marine-derived thioalkaloids
4
dassonmycins biomimetic
4
synthesis marine
4
marine thioalkaloids
4
dassonmycins reported
4
reported synthesis
4
synthesis features
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!