Original scientific paper

Efficient Synthesis of the Components of the German Cockroach Sex Pheromone I

Gabor Baan ; Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1025 Budapest, Hungary
Lajos Novak ; Institute for Organic Chemistry, Technical University of Budapest, H-1111 Budapest, Hungary
Attila Kis-Tamas ; EGIS Pharmacochemical Works, H-1475 Budapest, Hungary
Csaba Szantay ; Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1025 Budapest, Hungary

Abstract

We wish to report ashort (6 steps) synthesis of sex pheromones
of the German cockroach, the 3,11-dimethyl-2-nonacosanone
(1) and the 29-hydroxy-3,11-dimethyl-2-nonacosanone (2)
using the halopolycarbon homologation as the key step. The
t-butyl-2-methyl-10-iodo-undecanoate (6) synthetized from 10-undecenoic acid (3) by methylation and iodination was coupled with
the Grignard reagent derived from stearyl bromide (7) and 18-
-bromooctadecanyl-tetrahidro-2-pyranyl ether (8) in the presenee
of dilithium tetrachlorocuprate. The natural pheromones (1 and
2) were finally obtained from the 2,10-dimethyl-octacosanon acid
derivatives (11 and 12) with methyllithium in 230/0 (1) and 16010
(2) overall yields.

Keywords

Hrčak ID:

177587

URI

https://hrcak.srce.hr/177587

Publication date:

16.5.1986.

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