P-32 Studies of Electrophilic Carbonyl Additions and the Synthesis of Isochroman Lactone Fragrances

Buller Hallway

Isochroman lactones are a rare class of musk odorants that have not received much attention from synthetic chemists. This is so despite reports indicating their ‘exceptional tenacity and stability in all media.’ They have also been reported as important intermediates in synthesis of bioactive alkaloids. However, there are very few methods currently developed for the synthesis of 1-substituted isochroman lactones. This presentation discusses our research that uses a one-pot tandem synthetic approach for preparation of these rare lactones. It involves an initial electrophilic carbonyl addition followed by an intramolecular Friedel Crafts cyclization. This work builds on years of experience in our lab, with both high school and undergraduate researchers, exploring and developing electrophilic carbonyl addition reactions. Our isochroman lactone preparation illustrates the synthetic power of this underutilized class of organic reactions.