Stereoselective Synthesis of a Versatile Intermediate for the Total Synthesis of Mono- and Bis-THF Containing Annonaceous Acetogenins.

Abstract Stereoselective synthesis of epoxy tetrahydrofuran (THF) 1 , a versatile synthetic precursor for mono-THF and bis-THF containing annonaceous acetogenins, is reported. Compound 1 was synthesized from tridecanal in 11 steps with an overall yield of 24%. The requisite configurations of the stereogenic centers in 1 were established by Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation. Formation of the THF-ring unit was accomplished by acid catalyzed epoxide ring opening and 5- exo cyclization reaction.