- Titanium(II)-based Z-reduction of alkynes: Stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes
-
A TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene skipped poly-ynes to the corresponding Z-dideuterio polyenes in a one-pot procedure with D2O as deuterium source is described, and this methodology (using H2O) is applied to the synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex attractant of Scrobipalpuloides absoluta, a destructive pest of tomatoes.
- Hungerford, Natasha L.,Kitching, William
-
-
Read Online
- A new and efficient synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone component of the tomato leafminer Tuta absoluta
-
An efficient synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone component of the tomato leafminer moth, Tuta absoluta, was accomplished. The synthesis started with but-3-yn-1-ol and gave an overall yield of 41%.
- Cabezas, Jorge A.
-
-
Read Online
- Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone
-
The major sex attractant released by Scrobipalpuloides absoluta, a devastating tomato pest, was identified as (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate by a novel strategy involving the random reduction of double bonds. The technique is applicable to double bond localization of polyunsaturated compounds available even in nanogram quantities. The triene ester was synthesized by a stereospecific procedure and shown to be highly attractive to conspecific males and identical to the natural substance.
- Attygalle, Athula B.,Jham, Gulab N.,Svatos, Ale,Frighetto, Rosa T. S.,Meinwald, Jerrold,Villela, Evaldo F.,Ferrara, Fernando A.,Uchoa-Fernandes, Manoel A.
-
-
Read Online
- Method for synthesizing master-tomato-moth pheromone
-
The invention discloses a synthetic method for female tomato hornworm pheromone. The synthetic method comprises the following steps: adopting (5Z,8Z)-undecadienal and diethyl 3-(tetrahydro-2H-pyran-2-yloxy)propylphosphonate to perform a wittig-hornor reaction s as to generate a compound 3 by taking butyl lithium as alkali; under the condition of taking p-TsOH-catalyzed methanol as a solvent, performing de-protection to generate a compound 4; and reacting the compound 4 with acetic anhydride to generate a compound a (3E, 8Z, 11Z)-14C-OAc by taking triethylamine as alkaline and taking dichloromethane as a solvent. Or, the synthetic method comprises the following steps: adopting a compound 5 and a compound 6 to perform a wittig-hornor reaction so as to generate the compound 3 by taking butyl lithium as alkali; performing de-protection to generate a chemical substance (3E, 8Z, 11Z)-tetradecatrieneacetate-1-alcohol under the catalysis of p-TsOH by taking the methanol as a solvent; and reacting the (3E, 8Z, 11Z)-tetradecatrieneacetate-1-alcohol with acetic anhydride to generate a chemical substance a by taking dichloromethane as the solvent and taking triethylamine as alkali. According to the synthetic method, high-risk high-pollution LiAlH4 and liquid ammonia are avoided, and the conversion rates of raw materials are improved.
- -
-
-
- Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
-
Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).
- Zubrytski,Kananovich,Matiushenkov
-
p. 813 - 823
(2017/08/02)
-
- An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta
-
A convenient new synthesis of the two pheromone components of the tomato pest Tuta absoluta in high overall yields and high stereoselectivity (30% yield, E,Z,Z 97% for the major compound and 23% yield, E,Z 99% for the minor component) is reported. The approaches compare favorably with others previously described.
- Puigmartí, Marc,Bosch, Ma Pilar,Guerrero, Angel
-
p. 961 - 968
(2015/03/30)
-
- 5-ACETOXY-(E3)-3-PENTENYL METHOXYMETHYL ETHER AND METHOD FOR PREPARING (E3)-3-ALKENYL ACETATE USING THE SAME
-
Provided are 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether which can be prepared in conventional reaction equipment and a method for preparing an (E3)-3-alkenyl acetate by using it. More specifically, 5-hydroxy-(E3)-3-pentenyl methoxymethyl ether obtained by reacting 4-formyl-(E3)-3-butenyl methoxymethyl ether with a reductant is reacted with an acetylating agent to prepare 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether. (E3)-3-alkenyl methoxymethyl ether obtained by a coupling reaction between the 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether and a Grignard reagent is treated with an acid, and then reacted with an acetylating agent to prepare the (E3)-3-alkenyl acetate.
- -
-
-
- Titanium(II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the sex pheromone of a tomato pest, Scrobipalpuloides absoluta
-
An operationally simple TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene 'skipped' polyynes to the corresponding Z-polyenes in a one-pot procedure is described and applied inter alia to the syntheses of deuterium labelled linolenic and oleic acids. Final quenching with D2O (instead of H2O) results in regio- and stereo-specific Z-dideuteration of the alkyne. The synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone of Scrobipalpuloides absoluta, a destructive pest of tomatoes, and the (3Z,8Z,11Z)-isomer, utilises this methodology in key reduction steps, and under- or over-reduction are negligible.
- Hungerford, Natasha L.,Kitching, William
-
p. 1839 - 1858
(2007/10/03)
-
- Tetradecatrienyl and tetradecadienyl acetates and their use as sex attractants for tomato pests
-
The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.
- -
-
-
- (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, major sex pheromone component of the tomato pest Scrobipalpuloides absoluta (Lepidoptera: Gelechiidae)
-
The major sex attractant emitted by Scrobipalpuloides absoluta females is shown to be (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate by a novel strategy involving the random reduction of double bonds, followed by methylthiolation of the reduced products. Each female sex gland contains ca. 1-5 ng of this pheromone. This triene ester, synthesized by a stereospecific procedure, shows spectral and gas chromatographic properties identical to those of the natural substance. In field tests and wind tunnel bioassays, the synthetic ester was found to be highly attractive to conspecific males. The male response to this pheromone, however, is restricted to the same early-morning time window during which females exhibit calling behavior.
- Attygalle, Athula B.,Jham, Gulab N.,Svatos, Ales,Frighetto, Rosa T. S.,Ferrara, Fernando A.,Vilela, Evaldo F.,Uchoa-Fernandes, Manoel A.,Meinwald, Jerrold
-
p. 305 - 314
(2007/10/03)
-
