A chemoenzymatic synthesis of hept-6-ene-2,5-diol stereomers: application to asymmetric synthesis of decarestrictine L, pyrenophorol, and stagonolide E.

Abstract

The stereomers of hept-6-ene-2,5-diol derivatives were conceived as useful chiral intermediates and were synthesized starting from sulcatol using two lipase-catalyzed acylation reactions as the key steps. The versatility of the intermediates was demonstrated by converting them to the titled tetrahydropyran, macrolide, and macrodiolide compounds using standard synthetic protocols.