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Conversion of Natural ( S )‐Bulbocapnine into Two (Ring A)‐Substituted Derivatives of ( R )‐Apomorphine
Author(s) -
Greecke Max,
Borer René,
Brossi Arnold
Publication year - 1979
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.19790620519
Subject(s) - chemistry , apomorphine , aporphine , stereochemistry , enantiomer , ring (chemistry) , methylenedioxy , diol , natural compound , alkaloid , organic chemistry , receptor , biochemistry , agonist , biochemical engineering , engineering , alkyl , halogen
(6a R )‐1,2‐(Methylenedioxy)aporphine‐10, 11‐diol ( 8 ) and (6a R )‐aporphine‐1, 1, 10, 11‐tetrol ( 16 ) have been prepared from natural ( S )‐bulbocapnine ( 4 ). For both compounds, the partial synthesis included racemic intermediates which have been resolved into their enantiomers. Both compounds 8 and 16 showed dopaminergic activity in rats, although to a lower extent than ( R )‐apomorphine ( 1 ) itself.