Abstract
The first synthesis of enhygrolide A, a scarce γ-alkylidenebutenolide antibiotic of the obligate marine myxobacterium Enhygromyxa salina, was achieved in five steps and 54% overall yield from tetronic acid. Key steps include (i) organocatalytic reductive alkylation, (ii) iron-catalyzed sp2-sp3 cross-coupling, and (iii) vinylogous aldol condensation. Aside from its brevity and reliance on environmentally sustainable processes, the synthesis demonstrates the serviceability of butenolide pivalates in cross-coupling reactions.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
4-Butyrolactone / analogs & derivatives*
-
4-Butyrolactone / chemical synthesis
-
4-Butyrolactone / chemistry
-
4-Butyrolactone / pharmacology
-
Aldehydes / chemistry
-
Alkylation
-
Anti-Bacterial Agents / chemical synthesis*
-
Anti-Bacterial Agents / chemistry
-
Anti-Bacterial Agents / pharmacology
-
Benzylidene Compounds / chemical synthesis*
-
Benzylidene Compounds / chemistry
-
Benzylidene Compounds / pharmacology
-
Catalysis
-
Marine Biology
-
Molecular Structure
-
Myxococcales / chemistry*
-
Stereoisomerism
Substances
-
Aldehydes
-
Anti-Bacterial Agents
-
Benzylidene Compounds
-
enhygrolide A
-
3-hydroxybutanal
-
butenolide
-
4-Butyrolactone