Synthesis of the grapevine moth sex pheromone by Grignard?Schlosser cross-coupling: The effect of the electrophile structure on the stereoisomeric ratio in the reaction products

Chrelashvili, Z. G.; Mavrov, M. V.; Dolidze, A. V.; Чижов, А. О.; Serebryakov, É. P.

doi:10.1007/bf00704206

Cited by 3 publications

(2 citation statements)

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“…Hydrogenation products, namely, conjugated E-enynic alcohols 537, can further be converted into E,Z-dienic alcohols 538. 475 In the case of propargyl compounds, the desired effect is also attained by transforming the alcohol into alcoholate with the subsequent addition of DIBAH, the reduction taking place within the ate-complex formed. 473 It is noteworthy that careful bromination of the reaction mixture carried out instead of the final hydrolysis in the reduction of the enynic alcohols 534 results in bromo-containing dienic alcohols 539 being formed as the major products; in this case, the configuration of double bonds is disturbed.…”

Section: CLmentioning

confidence: 99%

Synthetic methodologies for carbo-substituted conjugated dienes

Васильев¹,

Serebryakov²

2001

Russ. Chem. Rev.

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We report the observation of changes in the wave turbulence properties of gravitycapillary surface waves due to a finite-depth effect. When the fluid depth is decreased, a hump is observed on the wave spectrum in the capillary regime at a scale that depends on the depth. The possible origin of this hump is discussed. In the gravity regime, the wave spectrum still shows a power law but with an exponent that strongly depends on the depth. A change in the scaling of the gravity spectrum with the mean injected power is also reported. Finally, the probability density function of the wave amplitude rescaled by its rms value is found to be independent of the fluid depth and to be well described by a Tayfun distribution.

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Section: CLmentioning

confidence: 99%

Synthetic methodologies for carbo-substituted conjugated dienes

Васильев¹,

Serebryakov²

2001

Russ. Chem. Rev.

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“…Different approaches have been reported for the synthesis of (3 E ,5 Z )-3,5-alkadienoic acids and alkadienoates. Most of these procedures involve partial reduction or isomerization of acetylenes as the steps to introduce the conjugated diene system ( 1 , − . They also use, as starting material, an adequate 2,4-dienoate, applying a one carbon homologation () or a deconjugative protonation in basic medium ( , ).…”

Section: Introductionmentioning

confidence: 99%

Concise Preparation of the (3E,5Z)-Alkadienyl System. New Approach to the Synthesis of Principal Insect Sex Pheromone Constituents

Ragoussis

Panopoulou

Ragoussis

2004

J. Agric. Food Chem.

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A new rapid and low-cost preparation of the (3E,5Z)-3,5-alkadienyl system, encountered in several insect pheromone constituents, was developed. Knoevenagel condensation of (E)-2-alkenals with ethyl hydrogen malonate in dimethyl sulfoxide, in the presence of a catalytic amount of piperidinium acetate, led to a mixture of geometrical isomers of ethyl 3,5-alkadienoates and ethyl 2,4-alkadienoates, from which the (3E,5Z)-3,5-alkadienoate was conveniently separated, by the use of urea inclusion complex formation. The importance of this procedure has been illustrated by the preparation of the (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) 1, the (3E,5Z)-3,5-dodecadienyl acetate 2, and the (3E,5Z)-3,5-tetradecadienyl acetate 3. These compounds are the main components of insect sex pheromones and constitute synthetic targets of considerable interest for the semiochemical community.

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