Premium
Aromatization of 1‐Benzyltetrahydroisoquinolines: Racemization of (−)‐( S )‐( N ‐nor)‐Reticuline
Author(s) -
Buchs Peter,
Brossi Arnold
Publication year - 1981
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.19810640310
Subject(s) - chemistry , isoquinoline , aromatization , racemization , yield (engineering) , papaverine , alkaloid , stereochemistry , organic chemistry , medicinal chemistry , catalysis , medicine , materials science , metallurgy
Aromatization in the series of optically active 1‐benzyltetrahydroisoquinolines has been accomplished with (—)‐( S )−( N ‐nor)‐reticuline ( 1b ) and analogs. Direct catalytic or chemical reduction of the isoquinoline 4 obtained could not be achieved in a practical way but 4 was converted into 1 in three steps ( 4 → 8 → 9 → 1 ), in 55% overall yield. Partial O ‐methylation of the isoquinoline 4 gave the isoquinoline alkaloid palaudine ( 5 ), before papaverine ( 6 ) was formed.