224. Note on Attempts to Prepare Ring-B Homomorphinan-6-ones by Grewe Cyclization from Octahydro-1-phenethylisoquinolines

Article abstract of DOI:10.1002/hlca.19850680806

Grewe cyclization of the N-formyl-protected octahydroisoquinolin-6-one 1 prepared by conventional chemistry did not afford the expected homomorphinanone.The exclusive reaction product obtained in good yield was the α,β-unsaturated N-formyloctahydroisoquinolin-6-one 2, further converted by acid hydrolysis into the crystalline octahydroisoquinolin-6-one 8.