Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C-O and C-C Bond Formation Reaction.

A highly stereoselective formal total synthesis of brevisamide is described that proceeds through a convergent pathway and utilizes our own tandem isomerization/C-O and C-C bond formation reaction as the key step to construct the trans-2,6-disubstituted dihydropyran ring system. Other significant reactions in this synthesis include an iodolactonization, a Crimmins-modified 'non-Evans' syn aldol reaction, and a Horner-Wadsworth-Emmons olefination. [ABSTRACT FROM AUTHOR]