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

preprint
submitted on 16.11.2018 and posted on 16.11.2018 by Thomas Siemon, Simon Steinhauer, Mathias Christmann
Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was 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 tetrahydrofurans. Here we describe the first synthesis of (+)-darwinolide featuring 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.

History

Email Address of Submitting Author

mathias.christmann@fu-berlin.de

Institution

Freie Universität Berlin

Country

Germany

ORCID For Submitting Author

0000-0001-9313-2392

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Submitted Version

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