A convergent synthesis of an analogue of salicylihalamide A with a six-member lactone ring was completed. The lactone ring was constructed through an automatic cyclization reaction and the two pieces were assembled together via Cu(I)-mediated amidation of vinyl iodide. Different methods of preparing the enamide side chain were explored as well. The obtained structure is aimed to answer important structure-and-activities questions regarding the biological mechanism of salicylihalamide A from an angle that has not been studied previously.
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Back to The 33rd Northeast Regional Meeting (July 14-17, 2005)