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Communication | Regular issue | Vol 27, No. 1, 1988, pp.45-48
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4337
Synthetic Approach to the Ivermectin Bottom Half Using Internal Cycloadducts of N-Furfuryl Acrylamides: Functionality and Optical Activity

Michael E. Jung* and Leslie J. Street

*Department of Chamistry and Biochemistry, University of California Los Angeles, Los Angels CA 90024, U.S.A.

Abstract

The 2-(α-benzyloxyacetyl) furan 2b is converted into the aminal 3b which undergoes intemal cycloaddition to give a highly oxidized intermediate 5b in a potential route to ivermectin 1, while the use of (S)-valinol in this sequence permits the ready preparation-separation of both enantiomers of 5a.