METHOD FOR EFFECTING THE EQUIVALENT OF A DEMAYO REACTION WITH FORMYL ACETIC ESTER

Both Woodward reserpine precursor 1 and Corey prostaglandin precursor 3 are monocyclic compounds with vicinal carboxaldehyde and acetic ester appendages. Disconnection of these appendages (along with disconnection of the two oxygen substituents of 1) generates hypothetical precursors (1,4-dihydrobenzoic acid and cis-cyclopentene-3,5-diol) both of which are readily available. Therefore, both reserpine and the prostaglandins might become available by short synthetic sequences if a method existed for the placement of vicinal carboxaldehyde and acetic ester appendages onto double bonds. This paper reports a five-step sequence that accomplishes this transformation for the case of 4-hydroxycyclohexene. © 1979, American Chemical Society. All rights reserved.