Synthesis of 6'-Methylated Reticulines and Tetrahydropapaverolines
Year: 1983
Type: article
Abstract: ~acemic 6'-merhylrericuline and the racemate and both enantimers of 6'-methyl-N-norreliculine and 6 ' -m e t h y l t e t r a h y d r o p a p ~~~~~l i n e were synthesized from the appropriate isomers of coreximine diacetate (1).Reduction OF crystalline chloromerhylcarbamare 2 wirh LAX gave (+)-6'-methylreficuline (5) directly.Hydrogenation (?)-? and the optical isomers followed by hydrazinolysis provided rhe correapondinp.6'-methyl-N-norreficulines (6, &, & I ) which were converted ro the racemate and enanriomers of 6'-merhyltetrahydropap~~eroline (8, &, &) by O-demefhylafion wirh 48% hydrobromic acid.The interaction of 1-benzyl-substituted ferrahydroisoquinolines (TIQ) and retrehydropapaverolines (THP) wifh dopaminergic and adrenergic receptors appears t o require specific molecular conforma-
Source: Heterocycles
Authors: Arnold Brossi, Padam N. Sharma, Kenner C. Rice
Language: English
Subfield: Cancer Research
Domain: Life Sciences
Open Access status: diamond
OpenAlex ID: W2083829259