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Volumn 29, Issue 9, 1990, Pages 1024-1025

Building Blocks for the Synthesis of Enantiomerically Pure Jasmonoids: Synthesis of (+)‐Methyl Epijasmonate

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EID: 33748225971     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199010241     Document Type: Article
Times cited : (48)

References (26)
  • 6
    • 84990163365 scopus 로고    scopus 로고
    • This compound, called “δ‐Jasmonsäurelacton” by its discoverers, was isolated from the oil of jasmine flowers:,. However, this paper gives the formula of the enantiomer of 2 (presumably arbitrarily)
    • Tetrahedron Lett. , vol.1977 , pp. 3413-3416
    • Kaiser, R.1    Lamparsky, D.2
  • 8
    • 84891300795 scopus 로고
    • (1983) Synform , vol.1 , pp. 33-63
  • 9
    • 84990163345 scopus 로고
    • 125–133
    • (1985) Synform , vol.3
  • 16
    • 84990147200 scopus 로고    scopus 로고
    • In order to determine the enantiomeric purity. 5 was treated with 1 (1‐naphthyl)ethylamine to give diastereomeric amides, which were analyzed by HPLC.
  • 20
    • 84990077737 scopus 로고    scopus 로고
    • Analogous derivatives 8, X = Cl, Br, OH, are also readily available in yields of about 80% by heating with aqueous mineral acids.
  • 23
    • 84990125935 scopus 로고    scopus 로고
    • A Z/E selectivity of ≥96:4 was achieved. Pure Z isomer, isolated by MPLC, was used in all further reactions.
  • 24
    • 84990144253 scopus 로고    scopus 로고
    • 3) for natural material of only 85% purity.
  • 25
    • 84990134949 scopus 로고    scopus 로고
    • 50‐cm column, Merck silica gel 60, 5 μ; eluent, n‐hexane/ethyl acetate 9:1; refractometer detector.
  • 26
    • 84990165932 scopus 로고    scopus 로고
    • Capillary columns, Hewlett Packard HP‐5 (25 m) and HP‐1 (5 m); temperature of injector, 220 and 180°C, respectively; temperature of column, 120–180 and 80°C, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.