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Proc Natl Acad Sci U S A ; 67(3): 1462-4, 1970 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-5274469

RESUMO

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.


Assuntos
Hormônios de Invertebrado/síntese química , Métodos , Estereoisomerismo
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