Iodo lactones 4 and 5 were prepared from m-anisic acid (10) and m-(isopropylthio)benzoic acid (15),respectively, by using a reductive alkylation-halolactonization-free radical cyclization sequence. Enones 6-9 were prepared from benzoic acid by way of acid chloride 30 by using a palladium-catalyzed coupling reaction. Tri-n-butyltin hydride mediated cyclization of 4-7 and 9 afforded substituted perhydronaphthalenes with good stereoselectivity. The radical derived from enone 8 gave perhydroindan 40. A transition-state geometry for the cyclization of enones 6-9 is proposed.
All Science Journal Classification (ASJC) codes
- Organic Chemistry