Nitro compounds in the double annulation route to trans-fused bicyclic compounds

Tethered carbon acids bearing nitro groups undergo a double Michael reaction with 3-butyn-2-one, and the cyclic products thereby obtained can be transformed into trans-fused bicyclic compounds with high levels of substitution and functionality. Three new C-C or C-N bonds, two new rings, two to four new stereocenters, and one or two new quaternary centers are created in this novel double annulation of two acyclic, readily available starting materials. Examples of the synthesis of trans-decalins, trans- hydrindanes, and trans-perhydroindoles are presented. Methods for converting the nitro groups in the double Michael and double annulation products into other groups are also described.