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Synlett 1996; 1996(7): 643-644
DOI: 10.1055/s-1996-5558
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Radical Mediated Macrocyclisation-Transannulation Cascades leading to Ring-fused Lactones and Lactams

Alexander J. Blake, Gregory J. Hollingworth, Gerald Pattenden*
  • *Department of Chemistry, Nottingham University, Nottingham NG7 2RD, England
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Publication Date:
31 December 2000 (online)

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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.

radical - cyclisation - cascade - lactam - lactone