4.8 Article

Synthesis of (+)-Darwinolide, a Biofilm-Penetrating Anti-MRSA Agent

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 4, Pages 1120-1122

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813142

Keywords

antibiotics; darwinolide; marine natural products; terpenoids; total synthesis

Ask authors/readers for more resources

Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was previously shown to exhibit promising activity against the biofilm phase of methicillin-resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven-membered core with two fused tetrahydrofuran units. Herein, we describe the first synthesis of (+)-darwinolide, which features a convergent aldol fragment coupling, an Ireland-Claisen rearrangement, and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm-specific antibiotics.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available