Aromatization of 1‐Benzyltetrahydroisoquinolines: Racemization of (−)‐( S )‐( N ‐nor)‐Reticuline | Zendy

Buchs Peter | Zendy; Brossi Arnold | Zendy

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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.

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