A Short Stereoselective Synthesis of Cecropia Juvenile Hormone
- 1 November 1970
- journal article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 67 (3) , 1462-1464
- https://doi.org/10.1073/pnas.67.3.1462
Abstract
A very short synthesis of the racemic cecropia hormone has been realized, utilizing a Claisen reaction. Methyl 6-hydroxy-3-methyl-7-methylene-2-trans-nonenoate, on treatment with the dimethyl ketal of 3-chloro-3-methyl-2-pentanone and a catalytic amount of 2,4-dinitrophenol, is transformed directly into methyl 11-chloro-3,11-dimethyl-7-ethyl-10-oxo-2-trans, 6-trans-tridecadienoate. Selective reduction gives a mixture of diastereoisomeric chlorohydrins separable by chromatography. The predominant threo-chlorohydrin is transformed into the juvenile hormone.Keywords
This publication has 2 references indexed in Scilit:
- Application of the Chloro Ketal Claisen Reaction to the Total Synthesis of SqualeneProceedings of the National Academy of Sciences, 1970
- Synthesis of Cecropia juvenile hormone from trans,trans-farnesolJournal of the American Chemical Society, 1970