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Synthesis of [β-4,5-3H]-cholestan-3-one, a trail following pheromone component of the eastern tent caterpillar

✍ Scribed by James P. DiBattista; Francis X. Webster

Publisher: John Wiley and Sons
Year: 1996
Tongue: French
Weight: 145 KB
Volume: 38
Category: Article
ISSN: 0022-2135
DOI: 10.1002/(sici)1099-1344(199612)38:12<1083::aid-jlcr931>3.0.co;2-y

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✦ Synopsis

Hydrogenation of 4-cholesten-3-one (1) with tritium gas over palladium black in pyridine afforded [P-4,5-SH]-cholestan-3-one (2a).

Tritium NMR showed that there was a mixture of tritiated compounds formed, 2a-2c; the latter two containing small amounts of protium substitution. Tritium NMR also indicated that none of the unwanted adiastereomer was formed.

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