The Transformation of Carvone into Racemic Grandisol
- 15 April 1974
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 52 (8) , 1352-1360
- https://doi.org/10.1139/v74-206
Abstract
Grandisol (1) is one of the components of the pheromone complex emitted by the male boll weevil. We report the transformation of readily available eucarvone (3), via the photoisomer 4, into grandisol in 20% overall yield. A key step in the synthesis is the Beckmann cleavage of oxime 15, derived in three steps from 4, to nitrite 16. Hydrolysis of 16 followed by hydride reduction gives grandisol (1).Keywords
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