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Volumn 29, Issue 44, 1988, Pages 5613-5616

An efficient cyclopentenone formation via an allene oxide

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Indexed keywords


EID: 0000853980     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)80826-6     Document Type: Article
Times cited : (48)

References (49)
  • 22
    • 0024284749 scopus 로고
    • The upfield shift (~0.5ppm) of the ring-juncture protons in the trans side chain configuration is also diagnostic: see, for example
    • (1988) Biochemistry , vol.27 , pp. 18
    • Baertschi1    Ingram2    Harris3    Brash4
  • 23
    • 84989111436 scopus 로고
    • Stereochemical aspects of proton chemical shifts. III—Configurational assignments in pentacyclic systems without recourse to a karplus equation
    • (1975) Organic Magnetic Resonance , vol.7 , pp. 345
    • Anteunis1    Danneels2
  • 24
    • 84918158898 scopus 로고    scopus 로고
    • The possibility of epimerization was strongly suggested by the observation that the trans/cis ratio of the product was dependent on the reaction time.
  • 30
    • 84918117473 scopus 로고
    • Unlike the rate-accelerating effect by the hydroxy group of vinyl allenes in the transition metal epoxidation treatment of vinyl allenes 1b-f (or corresponding alkoxy derivatives) with peracids may result in preferential epoxidation on the vinyl portion of the molecules., Cf.,Paris, Ser. C
    • (1967) Acad. Sci. , vol.265 , pp. 196
    • Bertrand1    Gore2
  • 40
    • 0023665336 scopus 로고
    • On non-cyclooxygenase prostaglandin synthesis in the sea whip coral, Plexaura homomalla: an 8(R)-lipoxygenase pathway leads to formation of an alpha-ketol and a Racemic prostanoid.
    • (1987) J Biol Chem , vol.262 , pp. 15829
    • Brash1    Baertschi2    Ingram3    Harris4
  • 49
    • 84918158896 scopus 로고    scopus 로고
    • It is tempting to speculate that the 11(S),13(S)-allene oxide derived from the 13(S)-hydroperoxide of linolenic acid would afford the racemic cis-12-oxophytodienoic acid via an oxypentadienyl cation pathway (ref. 13). On the other hand, the diastereomeric 11(R),13(S)-allene oxide may undergo the ring closure in a concerted pathway, resulting in the enantioselective formation of the cyclopentenone (ref. 15), but the mechanism of the chirality transfer remains unclear.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.