Premium
Selective Ether Cleavage in the Aporphine Series. Conversion of ( S )‐Bulbocapnine into ( S )‐Corytuberine and ( S )‐Corydine Methyl Ether
Author(s) -
Gerecke Max,
Borer René,
Brossi Arnold
Publication year - 1976
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.19760590731
Subject(s) - chemistry , ether , ether cleavage , stereochemistry , derivative (finance) , diol , organic chemistry , medicinal chemistry , financial economics , economics
Bulbocapnine methyl ether ( 2 ), on treatment with boron halides, affords the aporphine‐1,2‐diol ( 3 ), the novel aporphines 5 and 6 or the phenanthrene derivative 11 depending on the reaction conditions. 3 can be further transformed into corydine methyl ether ( 4 ); 6 has been converted to corytuberine ( 8 ). Similarly, dehydrobulbocapnine methyl ether 9 was converted to 10 .