Literature DB >> 17971751

A simple and cost effective synthesis of 3,11-dimethylnonacosan-2-one, a female sex pheromone of the German cockroach.

Kwang-Chan Ahn1, Jae-Chul Jung, Oee-Sook Park.   

Abstract

A convenient synthesis of 3,11-dimethylnonacosan-2-one (1) is described. Our strategy involves the use of well known C-alkylation and ethyl acetoacetate synthesis reactions as key steps. We expect that this method will prove to be useful for large scale preparation of 1 and modification of dimethylnonacosanones.

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Year:  2006        PMID: 17971751      PMCID: PMC6148567          DOI: 10.3390/11100751

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  7 in total

1.  A direct retro-barbier fragmentation

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

2.  Synthesis of 3,11-dimethyl-2-nonacosanone, a contact courting pheromone of the German cockroach.

Authors:  A W Burgstahler; L O Weigel; W J Bell; M K Rust
Journal:  J Org Chem       Date:  1975-11-14       Impact factor: 4.354

3.  Concise and efficient asymmetric synthesis of (S)-2-ethylphenylpropanoic acid derivatives: dual agonists for human peroxisome proliferator-activated receptor alpha and delta.

Authors:  Jun-ichi Kasuga; Yuichi Hashimoto; Hiroyuki Miyachi
Journal:  Bioorg Med Chem Lett       Date:  2006-02-15       Impact factor: 2.823

4.  Biosynthesis and endocrine control of the production of the German cockroach sex pheromone 3,11-dimethylnonacosan-2-one.

Authors:  J Chase; K Touhara; G D Prestwich; C Schal; G J Blomquist
Journal:  Proc Natl Acad Sci U S A       Date:  1992-07-01       Impact factor: 11.205

5.  Behavioral activity of stereoisomers and a new component of the contact sex pheromone of female German cockroach, Blattella germanica.

Authors:  Dorit Eliyahu; Kenji Mori; Hirosato Takikawa; Walter S Leal; Coby Schal
Journal:  J Chem Ecol       Date:  2004-09       Impact factor: 2.626

6.  Patterns of biosynthesis and accumulation of hydrocarbons and contact sex pheromone in the female German cockroach, Blattella germanica.

Authors:  C Schal; X Gu; E L Burns; G J Blomquist
Journal:  Arch Insect Biochem Physiol       Date:  1994       Impact factor: 1.698

7.  Sex pheromone of the German cockroach (Blattella germanica L.) responsible for male wing-raising: 3,11-dimethyl-2-nonacosanone.

Authors:  R Nishida; H Fukami; S Ishii
Journal:  Experientia       Date:  1974-09-15
  7 in total
  1 in total

1.  Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica.

Authors:  Dorit Eliyahu; Satoshi Nojima; Sonja S Capracotta; Daniel L Comins; Coby Schal
Journal:  Naturwissenschaften       Date:  2008-01-09
  1 in total

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