Transannular Reactions of Peptides. The Peptide Nitrogen in a 10-Membered Ring1, 2

LA Cohen, B Witkop

Index: Cohen; Witkop Journal of the American Chemical Society, 1955 , vol. 77, p. 6595,6599

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Citation Number: 56

Abstract

In the ten-membered lactam VI11 prepared by spontaneous rearrangement of the hydroperoxide VI1 of A'@)-octahydroquinoline (IV) the nitrogen atom is sufficiently close to the ketone carbonyl to permit formation of a carbinolamine IX as the only stable modification. The structure of IX has been proved by exhaustive reduction with lithium aluminum hydride to the known base l-azabicyclo [5.3. 0] decane (XIII). Upon catalytic reduction, IX loses its ...