Insect Sex Attractants. VII. 5,9-Tridecadien-1-ol Acetates

1967 ◽  
Vol 10 (6) ◽  
pp. 1190-1191 ◽  
Author(s):  
David. Warthen ◽  
Martin. Jacobson
Keyword(s):  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Insect Sex

Insect Sex Attractants. I. The Isolation, Identification, and Synthesis of the Sex Attractant of the Gypsy Moth1

1961 ◽  
Vol 83 (23) ◽  
pp. 4819-4824 ◽  
Author(s):  
Martin Jacobson ◽  
Morton Beroza ◽  
William A. Jones
Keyword(s):  
Sex Attractant ◽  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Insect Sex

Insect sex attractants. X. 5-Dodecen-1-ol acetates, analogs of the cabbage looper sex attractant

1968 ◽  
Vol 11 (2) ◽  
pp. 373-374 ◽  
Author(s):  
David Warthen ◽  
Martin Jacobson
Keyword(s):  
Sex Attractant ◽  
Cabbage Looper ◽  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Insect Sex

Synthesis of insect sex attractants on solid phases

1976 ◽  
pp. 251 ◽  
Author(s):  
Clifford C. Leznoff ◽  
Thomas M. Fyles
Keyword(s):  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Solid Phases ◽  
Insect Sex

Purification and analysis of synthetic insect sex attractants by liquid chromatography on a silver-loaded resin

1974 ◽  
Vol 96 (1) ◽  
pp. 25-32 ◽  
Author(s):  
N.W.H. Houx ◽  
S. Voerman ◽  
W.M.F. Jongen
Keyword(s):  
Liquid Chromatography ◽  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Loaded Resin ◽  
Insect Sex

Insect Sex Attractants. II. The Synthesis of a Highly Potent Gypsy Moth Sex Attractant and Some Related Compounds1

1962 ◽  
Vol 27 (7) ◽  
pp. 2523-2524 ◽  
Author(s):  
Martin Jacobson ◽  
William A. Jones
Keyword(s):  
Gypsy Moth ◽  
Sex Attractant ◽  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Insect Sex

The use of polymer supports in organic synthesis. XII. The total stereoselective synthesis of cis insect sex attractants on solid phases

1977 ◽  
Vol 55 (23) ◽  
pp. 4135-4143 ◽  
Author(s):  
Thomas M. Fyles ◽  
Clifford C. Leznoff ◽  
John Weatherston
Keyword(s):  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Ethyl Bromide ◽  
Butyl Bromide ◽  
Sex Attractants ◽  
Polymer Supports ◽  
Acid Cleavage ◽  
Insect Sex Attractants ◽  
Internal Alkynes ◽  
Insect Sex

A 2% crosslinked divinylbenzene-styrene copolymer, incorporating trityl chloride groups (2) was used in the synthesis of insect sex attractants of Lepidoptera by a two-step alkyne coupling route. Polymer 2 reacted with the symmetrical diols, 1,8-octanediol and1,10-decanediol, to give the monoblocked polymer-bound diols 5 and 6 respectively. Mesylation of 5 and 6 gave the polymer-bound monomesylates 7 and 8 which on coupling with lithioacetylide gave the polymer-bound terminal alkynes 9 and 10 respectively. Acid cleavage of 9 and 10 provide 9-decyn-1-ol and 11-dodecyn-1-ol respectively. A second coupling step was performed by lithiation of 9 and 10 with n-butyllithium or tert-butyllithium followed by treatment with n-butyl bromide or ethyl bromide to give polymer-bound internal alkynes, which on acid hydrolysis gave 9-tetradecyn-1-ol (22), 11-hexadecyn-1-ol (23), and 11-tetradecyn-1-ol (24). If 10 had been lithiated with n-butyllithium and coupled with ethyl bromide, some translithiation occurred to liberate n-butyl bromide which entered into the coupling reaction eventually giving a mixture of 23 and 24. This problem was resolved by the use of tert-butyllithium in the lithiation step. Attempts were made to reduce polymer-bound internal alkynes stereoselectively to cis-alkenes with 9-borabicyclononane, diisobutylaluminum hydride, and catechol borane but all these reagents proved inadequate due to incomplete reduction, overreduction, hydrogenolysis of the alkyne from the polymer, and non-selectivity. Polymer-bound internal alkynes were quantitatively reduced exclusively to cis insect sex attractants using disiamylborane without concurrent overreduction or hydrogenolysis.

Bifunctionalized resins. Applications to the synthesis of insect sex attractants

1978 ◽  
Vol 56 (7) ◽  
pp. 1031-1041 ◽  
Author(s):  
Thomas M. Fyles ◽  
Clifford C. Leznoff ◽  
John Weatherston
Keyword(s):  
Benzoic Acid ◽  
Benzoyl Chloride ◽  
Wittig Reaction ◽  
Solution Phase ◽  
Sex Attractants ◽  
Styrene Copolymer ◽  
Random Array ◽  
Insect Sex Attractants ◽  
Insect Sex

A 2% crosslinked divinylbenzene–styrene copolymer, incorporating benzoyl chloride groups, was used to monoprotect the symmetrical diol 1,10-decanediol. The corresponding monotrityl ether and cis-10-tetradecen-1-ol were prepared by this system, the latter by a Wittig reaction of a polymer-bound ylide with an aldehyde in the solution phase. A series of bifunctionalized resins containing proximally located trityl alcohol and benzoic acid groups was prepared in an attempt to prepare diol linked to the polymer via both a trityl ether and a benzoate linkage. It was established that these polymers bound 1,10-decanediol exclusively at one end only. Polymers, containing both trityl alcohol and benzoic acid groups in a random array or polymers containing proximally located trityl alcohol groups, gave mixtures of both monoprotected and doubly protected diol.

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