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Volumn 45, Issue 2, 2004, Pages 239-241

Unsymmetrical double Wittig olefination on the syntheses of insect pheromones. Part 1: Synthesis of 5,9-dimethylpentadecane, the sexual pheromone of Leucoptera coffeella

Author keywords

5,9 Dimethylpentadecane; 7,11 Dimethylheptadecane; 7 Methylheptadecane; Cuticular hydrocarbons; Double Wittig reaction; Leucoptera coffeella; Pheromone; Synthesis

Indexed keywords

1,3 DIBROMOPROPANE; 2 HEXANONE; 2 OCTANONE; 5,9 DIMETHYLPENTADECANE; ALKADIENE; ALKANE DERIVATIVE; KETONE DERIVATIVE; PHEROMONE DERIVATIVE; PHOSPHONIUM DERIVATIVE; SEX PHEROMONE; UNCLASSIFIED DRUG;

EID: 0347627373     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.183     Document Type: Article
Times cited : (21)

References (19)
  • 1
    • 0003980030 scopus 로고
    • The Biosynthesis of Secondary Metabolites
    • London: Chapman & Hall
    • Herbert R.B. The Biosynthesis of Secondary Metabolites. 2nd ed. 1989;Chapman & Hall, London.
    • (1989) 2nd Ed.
    • Herbert, R.B.1
  • 2
    • 0000416205 scopus 로고
    • The Synthesis of Insect Pheromones
    • J. ApSimon. New York: John Wiley & Sons
    • Mori K. ApSimon J. The Synthesis of Insect Pheromones. The Total Synthesis of Natural Products. Vol. 9:1992;John Wiley & Sons, New York.
    • (1992) The Total Synthesis of Natural Products , vol.9
    • Mori, K.1
  • 9
    • 85030927044 scopus 로고    scopus 로고
    • note
    • The manuscript describing a complete data set of field experiments is now in progress and will appear elsewhere.
  • 11
    • 85030922582 scopus 로고    scopus 로고
    • note
    • -1 in hexane), and the reaction mixture was allowed to warm to room temperature, stirred for additional 30 min and re-cooled (-90 °C). A solution of the first carbonyl component (1.0 mmol) in THF (1.0 mL) was added dropwise, and the mixture was allowed to reach room temperature, stirred for additional 30 min and re-cooled (-90 °C). The same protocol was adopted to generate the second ylide (1.1 equiv n-BuLi) and to the addition of the second carbonyl component (1.0 equiv). Usual work-up and flash chromatography on silica gel yielded the respective dienes.
  • 13
    • 85030925250 scopus 로고    scopus 로고
    • note
    • The reactivity of ketones and aldehydes with the monoylides under the reaction condition described above is quite similar, and the ratio of the symmetric coupling by-products obtained is almost the same.
  • 18
    • 85030931663 scopus 로고    scopus 로고
    • note
    • This compound was proved as highly efficient in capturing males of coffee leaf miner in the field. The manuscript is in preparation.
  • 19
    • 85030927887 scopus 로고    scopus 로고
    • note
    • It is quite difficult to separate the symmetrical products 1a and 1b to the unsymmetrical 1 by conventional methods. However, in the cases that the carbonyl sources differs in more than four carbon atoms, a carefully distillation allow the purification.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.