Radical Mediated Macrocyclisation-Transannulation Cascades leading to Ring-fused Lactones and Lactams

Abstract
Treatment of the iodoalkenyl acrylamides 1, 3 and 5 and the acrylates 7, 10 and 12 with Bu3SnH-AIBN leads to ring fused lactams 2, 4, 6 and lactones 8, 9 and 11 respectively, by way of diastereoselective cascade macrocyclisation-transannulation pathways. In a similar manner the ynoate 13 undergoes cyclisation to the unsaturated bicyclic lactone 14.

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