A new stereoselective synthesis of racemic disparlure, the sex pheromone of gypsy moth ( L.)

Толстиков, Г. А.; Odinokov, V. N.; Галеева, Р. И.; Bakeeva, R. S.

doi:10.1016/s0040-4039(01)94690-8

Cited by 22 publications

(4 citation statements)

References 6 publications

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“…Transformation of activated derivatives of alcohol 8 to isobutyl 11 was attempted with i PrMgCl. However, the tosylate, the bromide, and the triflate derivatives did not react with i PrMgCl. Therefore, alcohol 8 was oxidized to aldehyde 9 which underwent a Wittig reaction .…”

Section: Resultsmentioning

confidence: 98%

Design, Synthesis, and Evaluation of the Multidrug Resistance-Reversing Activity of d-Glucose Mimetics of Hapalosin

Dinh

Smith

et al. 1998

J. Med. Chem.

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When five substituents of hapalosin were placed on D-glucose, molecular modeling revealed that the substituents on mimetics 2 and 3 occupy similar spatial positions as the corresponding substituents on hapalosin. Mimetic 3 and all the glucopyranoside intermediates generated in its synthesis were assessed for their ability to reverse multidrug resistance (MDR) mediated by P-glycoprotein (P-gp) or the multidrug resistance-associated protein (MRP). None of the sugar compounds were as effective as hapalosin in inhibiting P-gp in cytotoxicity and drug accumulation assays using MCF-7/ADR cells. By contrast, four D-glucose compounds exhibited similar efficacy as hapalosin in antagonizing MRP in cytotoxicity assays with HL-60/ADR cells.

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Section: Resultsmentioning

confidence: 98%

Design, Synthesis, and Evaluation of the Multidrug Resistance-Reversing Activity of d-Glucose Mimetics of Hapalosin

Dinh

Smith

et al. 1998

J. Med. Chem.

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“…While alkene 6 is commercially available, alkenes 7 − 9 were prepared by an S N 2 displacement reaction using 4-bromobenzyl bromide and the appropriate Grignard reagent (eq 1). For the syntheses of alkene 8 and 9 , a catalytic amount of lithium tetrachlorocuprate(II) was required (eq 1) . Cyclobutanones were obtained (Scheme ) via a 2 + 2 cycloaddition of the precursor alkenes with dichloroketene, which was generated in situ from the reaction of trichloroacetyl chloride and phosphorus oxychloride in the presence of a Zn−Cu couple .…”

Section: Resultsmentioning

confidence: 99%

“…For the syntheses of alkene 8 and 9, a catalytic amount of lithium tetrachlorocuprate(II) was required (eq 1). 33 Cyclobutanones were obtained (Scheme 1) via a 2 + 2 cycloaddition of the precursor alkenes with dichloroketene, which was generated in situ from the reaction of trichloroacetyl chloride and phosphorus oxychloride in the presence of a Zn-Cu couple. 34 The crude products (dichlorocyclo-butanones 10-13) obtained from the ketene additions were subjected to a reductive dechlorination with zinc and acetic acid.…”

Section: Resultsmentioning

confidence: 99%

4-Dihydroxyborylphenyl Analogues of 1-Aminocyclobutanecarboxylic Acids: Potential Boron Neutron Capture Therapy Agents

1999

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A series of 4-dihydroxyborylphenyl analogues of an unnatural α-amino acid, 1-aminocyclobutanecarboxylic acid (ACBC), was synthesized. Varying numbers of methylene units were introduced between the 4-boronophenyl and ACBC moieties in order to introduce different degrees of lipophilicity into the molecules. The key step in the syntheses was the preparation of the precursor p-boronophenyl-substituted cyclobutanones which were subsequently converted to the desired amino acids via the Bucherer−Strecker reaction.

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“…[19] Multiple reported syntheses of (±)- 24 exist and require no fewer than four steps. [5h,20] Our synthesis was carried out as shown in Scheme 6. First, cross metathesis of 4-pentenol and 1-dodecene afforded 21 in moderate yield (62%) and high Z -selectivity (84%).…”

mentioning

confidence: 99%

Concise Syntheses of Insect Pheromones Using Z‐Selective Cross Metathesis

et al. 2012

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The shortest synthetic routes to nine cis-pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported. These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z-olefins. Important insight into the mechanism of Z-selective metathesis was uncovered during experimentation and subsequently explored.

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A new stereoselective synthesis of racemic disparlure, the sex pheromone of gypsy moth ( L.)

Cited by 22 publications

References 6 publications

Design, Synthesis, and Evaluation of the Multidrug Resistance-Reversing Activity of d-Glucose Mimetics of Hapalosin

Design, Synthesis, and Evaluation of the Multidrug Resistance-Reversing Activity of d-Glucose Mimetics of Hapalosin

4-Dihydroxyborylphenyl Analogues of 1-Aminocyclobutanecarboxylic Acids: Potential Boron Neutron Capture Therapy Agents

Concise Syntheses of Insect Pheromones Using Z‐Selective Cross Metathesis

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