Benzylidene-directed endo cyclization of epoxy alcohols

ORGN 49

Aaron R. Van Dyke, vandya@mit.edu and Timothy F. Jamison. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Room 18-223, Cambridge, MA 02139
Most methods for the intramolecular cyclization of epoxy alcohols to form tetrahydropyran rings electronically modify the epoxide to favor the desired regioisomer. Recently we have found that benzylidene acetals direct the desired endo cyclization without the need for biasing the epoxide in this fashion. Details of this transformation and a discussion of its potential application to the synthesis of polyether natural products will be presented.