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Note on Attempts to Prepare Ring‐B Homomorphinan‐6‐ones by Grewe Cyclization from Octahydro‐1‐phenethylisoquinolines
Author(s) -
Dumont Raymond,
Pfander Hanspeter,
Brossi Arnold
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680806
Subject(s) - chemistry , yield (engineering) , ring (chemistry) , hydrolysis , product (mathematics) , medicinal chemistry , stereochemistry , organic chemistry , geometry , mathematics , materials science , metallurgy
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 .