Back to Table of Contents

43546-G1
An Enyne Metathesis Strategy for the Synthesis of Medium-Sized Ring-Containing Icetaxane Diterpenoids

Richmond Sarpong, University of California (Berkeley)

In a continuation of our work from the previous grant period, we have applied our Ga(III)-catalyzed cycloisomerization reaction to the synthesis of other, more complex icetexane diterpenoid natural products. The natural products brussonol, hydroxysalviasperanol and abrotanone were synthesized using this strategy. These total syntheses enabled an unequivocal reassignment of the correct relative stereochemistry of abrotanone, which had been previously misassigned. The synthetic strategies that we developed have also spurred the investigation of several cycloisomerization side reactions which will be exploited for complex molecule synthesis. Furthermore, the Ga(III)-catalyzed cycloisomerization chemistry is proving to be a general strategy that may be applied to other seven-membered ring containing natural products including rearranged steroidal alkaloids.

Back to top