Total Synthesis of (–)-Sinulariadiolide
Total Synthesis of (–)-Sinulariadiolide. A Transannular Approach.
J. Am. Chem. Soc. 2019;
15 February 2019 (online)
Key words(–)-sinulariadiolide - Eschenmoser–Tanabe fragmentation - ring-closing alkyne metathesis - trans-hydrostannation - Michael addition
The tricyclic nor-cembranoid sinulariadiolide was first isolated in 1996 from soft corals found in Okinawa. Fürstner and Meng report the total synthesis of (–)-sinulariadiolide via ring-closing alkyne metathesis followed by an intriguing intramolecular reaction cascade.
Fragments E and H were accessed from geranic acid (A) and carvone (F). Ring-closing alkyne metathesis and hydrostannation–carbonylation of J gave N. The title compound was accessed by a sequence involving transannular Michael addition.