Tetrahedron Letters p. 9309 - 9312 (1998)
Update date:2022-08-04
Topics:
Derrer, Sam
Feeder, Neil
Teat, Simon J.
Davies, John E.
Holmes, Andrew B.
As part of a project evaluating medium-ring lactams as constrained peptidomimetics, a novel method for the formation of multisubstituted eight- membered lactams has been developed. N-Protected 7-amino-8-hydroxy-octenoic acids were cyclised to give 8-amino-5,6-dehydro-2-oxocanones which underwent clean intramolecular O-to-N-acyl (lactone-to-lactam) ring contraction to yield 8-hydroxymethyl-6,7-dehydro-2-azocanones, suitable for elaboration to eight-membered lactam dipeptides.
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