Formal Total Synthesis of cis-Sylvaticin and Sylvaticin

Formal total synthesis of Annonaceae acetogenin natural products cis-sylvaticin and sylvaticin was accomplished from a C2-symmetric furyl carbinol. The key reaction in the synthesis is the use of furan as a but-2-ene-1,4-dione synthon, a Donohoe variant of osmium-catalyzed synthesis of 2,5-cis-substituted tetrahydrofuran, and a Mukaiyama oxidative cyclization for the formation of trans-2,5-disubstitued tetrahydrofuran.