Following stereoselective addition of N-iodosuccinimide towards glycals and subsequent dehalogenation, glycosylimides 1 and 2 are obtained and converted by irradiation to yield the azepindione derivatives 3 and 4 and the [5.3.1.02,6] tricyclic alcohols 5 and 6; their prolonged irradiation gives highly functionalised bridged heterotricyclic lactams 10 and 11 with a cyclopentane backbone.
C. E. Sowa, J. Kopf and J. Thiem, J. Chem. Soc., Chem. Commun., 1995, 211 DOI: 10.1039/C39950000211
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