Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes.

An efficient approach to the synthesis of perinaphthenones via the rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with internal alkynes was developed. Norbornadiene can act as an acetylene equivalent to give unsubstituted perinaphthenones at the 2- and 3-positions via dehydrative annulation followed by a retro Diels-Alder reaction.