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Total Synthesis of (-)-Sinulariadiolide. A Transannular Approach
Zhanchao Meng1, Alois Fürstner1
1Max-Planck-Institut für Kohlenforschung , 45470 Mülheim/Ruhr , Germany.
Abstract:
The constrained tricyclic skeleton of the nor-cembranoid sinulariadiolide (1) with a nine-membered nexus was obtained by a cascade of transannular Michael reaction, carbonate elimination, butenolide formation, and spontaneous oxa-Michael addition of MeOH. The required macrocyclic precursor was prepared by ring-closing alkyne metathesis followed by trans-hydrostannation/carbonylation.
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