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The synthesis of thebaine-1-3H

✍ Scribed by Satish C. Choudhry; Lucia Serico; Joseph Cupano; David H. Malarek; Arnold A. Liebman

Publisher: John Wiley and Sons
Year: 1989
Tongue: French
Weight: 250 KB
Volume: 27
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580271207

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✦ Synopsis

A synthesis of thebaine is described where the C-1 position is labelled with tritium to specific activity of 16 Ci/mmole. From codeine (a, 1iodocodeine ( 1 ) was prepared and converted to 1-iodothebaine (T, in 3 steps. The subsequent key reaction was the selective hydrogenolysis of the carbon-iodine bond in 1 in the presence of the dienic-enol ether system.

Using 10% Pd/C as catalyst, the desired reaction occurs in about 80% yield.

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