Total Synthesis of Scabrolide F

The first total synthesis of scabrolide F, a norcembranolide isolated from the soft coral Sinularia scabra, is described. Hydroxycarboxylic acid, which is the key synthetic intermediate, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was subjected to macrolactonization and subsequent transannular ring-closing metathesis (RCM) to furnish scabrolide F. The synthetic protocol can be extended to the total synthesis of other norcembranolides.

Automated summary

The first total synthesis of scabrolide F, a norcembranolide isolated from Sinularia scabra, a soft coral, is described. The key synthetic intermediate, hydroxycarboxylic acid, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was then subjected to macrolactonization and subsequent transannular RCM to obtain scabrolide F. This synthetic protocol can be extended to the total synthesis of other norcembranolides.