52207-99-5Relevant academic research and scientific papers
Ti-catalyzed cross-cyclomagnesiation of 1,2-dienes in the stereoselective synthesis of insect pheromones
D'yakonov, Vladimir A.,Islamov, Ilgiz I.,Makarov, Aleksey A.,Dzhemilev, Usein M.
supporting information, p. 1755 - 1757 (2017/04/13)
The Ti-catalyzed intermolecular cross-cyclomagnesiation reaction of aliphatic and oxygenated 1,2-dienes with Grignard reagents was used as the key step to develop facile stereoselective methods for preparation of the major components of citrus leafminer moth (Phyllocnistis citrella) pheromones as well as cotton pink bollworm (Pectinophora gossypiella) and fruit fly (Drosophila melanogaster) attractants.
STEREOSPECIFIC SYNTHESIS OF COMPONENTS OF THE NATURAL SEX PHEROMONE OF Pectinophora gossypiella
Matveeva, E. D.,Kvasha, M. P.,Kurts, A.L.
, p. 1017 - 1021 (2007/10/02)
A multistage stereospecific synthesis of components of the natural pheromone was realized.Conditions were found for stereospecific trans-reduction of the triple bonds.A procedure was developed for regiospecific dehydrohalogenation of 1,2-dibromoalkanes.Conditions giving the Z and E isomers in ratio of 96 : 4 were found for the Wittig reaction.
OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS XL. SYNTHESIS OF (Z,Z)-, (E,E)-, AND (E/Z,Z/E)-7,11-HEXADECADIEN-1-YL ACETATES - COMPONENTS OF THE SEX PHEROMONE OF PECTINOPHORA GOSSYPIELLA (SAUNDERS)
Odinokov, V. N.,Mukhametzyanova, R. S.,Galeeva, R. I.,Ishmuratov, G. Yu.,Tolstikov, G. A.
, p. 1399 - 1407 (2007/10/02)
A new approach is proposed for the synthesis of (Z,Z)-, (E,E)-, and (E/Z,Z/E)-7,11-hexadecadien-1-yl acetates, which are components of the sex pheromone of the pink bollworm (Pectinophora Gossypiella).The method is based on the selective ozonolysis of (Z,Z,Z)-, (E,E,E), and (E,E,Z)-cyclododecatrienes.
A Practical Synthesis of Sex Pheromones of Pink Bollworm: Gossyplure
Yadav, J. S.,Upender, V.,Shekharam, T.,Reddy, E. Rajarathnam
, p. 1012 - 1014 (2007/10/02)
The practical synthesis of (Z,Z) and (Z,E)-7,11-hexadecadienyl acetates, sex pheromones of pink bollworm (gossyplure) is described.
SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECT ATTRACTANTS (SEX ATTRACTANTS). X. SYNTHESIS OF THE ACETATES OF CIS-7,CIS-11- AND CIS-7,TRANS-11-HEXADECADIEN-1-OL, THE SEX PHEROMONES OF THE PINK BOLLWORM MOTH Pectinophora gossypiella S. (LEPIDOPTERA, GELECHIIDAE) AND THE GRAIN MOTH Sit...
Kovalev, B. G.,Avdeeva, L. A.,Sorochinskaya, A. M.
, p. 641 - 646 (2007/10/02)
The synthesis of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol, which are the sex pheromones of the pink bollworm moth Pectinophora gossypiella and the Angoumois grain moth Sitotroga cerealella, and their geometric isomers on the basis of the Wittig reaction and of the unsaturated functionally ω-substituted aldehydes is described.The alkylation of the dilithium derivative of 4-pentyn-1-ol by 2-(6-bromohexyloxy)tetrahydropyran in a mixture of liquid ammonia and THF gave a 40percent yield of 11-(2-tetrahydropyranyloxy)-4-undecyn-1-ol, which was hydrogenated selectively to 11-(2-tetrahydropyranyloxy)-cis-4-undecen-1-ol or was reduced to 11-(2-tetrahydropyranyloxy)-trans-4-undecen-1-ol.Both alcohols were oxidized by pyridinium chlorochromate to 11-(2-tetrahydropyranyloxy)-cis-4-undecenal and 11-(2-tetrahydropyranyloxy)-trans-4-undecenal.The reaction of both aldehydes with amyltriphenylphosphonium bromide under stereocontrolled conditions followed by acetolysis gave the acetates of cis-7,cis-11-, cis-7,trans-11-, trans-7,cis-11-, and trans-7,trans-11-hexadecadien-1-ols and a mixture of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol (gossyplure).
