Novel Opiates and Antagonists. 6. 7-Alkyl-6,7-didehydromorphinans

Article abstract of DOI:10.1021/jm00371a013

A method for preparing a variety of 7-alkyl-6,7-didehydromorphinans from the corresponding 6-morphinanones is described.The key intermediates in this sequence are the 7-formyl derivatives.The two epimeric B/C-trans-7-(1-hydroxypentyl)morphinans (16a, b) are stereochemically similar to the endo-ethanotetrahydrooripavines and are extremely potent in the mouse writhing test.The corresponding B/C-cis-7-(1-hydroxypentyl)morphinans are inactive in this test.