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Volumn 65, Issue 25, 2009, Pages 4808-4813

Novel rearrangement reaction of a 6,14-endoethanomorphinan derivative to a benzomorphan derivative

Author keywords

Benzomorphan; Fragmentation; Morphinan; Rearrangement

Indexed keywords

ACID ANHYDRIDE; ANALGESIC AGENT; BENZOMORPHAN DERIVATIVE; LACTONE; MORPHINAN DERIVATIVE; PENTAZOCINE; TOLUENE; TRIFLUOROMETHANESULFONIC ACID; TRIPHENYLTETRAZOLIUM;

EID: 65549147627     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.055     Document Type: Article
Times cited : (7)

References (39)
  • 7
    • 65549111041 scopus 로고    scopus 로고
    • We have already reported some rearrangement reactions of morphinan derivatives
    • We have already reported some rearrangement reactions of morphinan derivatives.
  • 17
    • 65549158987 scopus 로고    scopus 로고
    • note
    • Fragmentation of a 7-acyl-6,14-endoethenotetrahydrothebaine derivative was also reported. See Ref. 6a.
  • 18
    • 0014443763 scopus 로고
    • 7-Methylidene derivative has been prepared by other methods: Hofmann degradation of 7-dimethylaminomethyl derivative or treatment of the tosylate of the corresponding primary alcohol with t-BuOK
    • 7-Methylidene derivative has been prepared by other methods: Hofmann degradation of 7-dimethylaminomethyl derivative or treatment of the tosylate of the corresponding primary alcohol with t-BuOK. Bentley K.W., Hardy D.G., Lewis J.W., Readhead M.J., and Rushworth W.I. J. Chem. Soc. C (1969) 826
    • (1969) J. Chem. Soc. C , pp. 826
    • Bentley, K.W.1    Hardy, D.G.2    Lewis, J.W.3    Readhead, M.J.4    Rushworth, W.I.5
  • 19
    • 0015263494 scopus 로고
    • Treatment of the 7-methylidene derivative having a 6,14-etheno bridge with perchloric acid gave another product {A figure is presented}
    • Treatment of the 7-methylidene derivative having a 6,14-etheno bridge with perchloric acid gave another product. Lewis J.W., and Readhead M.J. J. Chem. Soc. C (1972) 881 {A figure is presented}
    • (1972) J. Chem. Soc. C , pp. 881
    • Lewis, J.W.1    Readhead, M.J.2
  • 22
    • 65549098525 scopus 로고    scopus 로고
    • For synthesis of pentazocine, see
    • For synthesis of pentazocine, see:
  • 29
    • 65549107188 scopus 로고    scopus 로고
    • For synthesis of, -pentazocine using optical resolution, see
    • For synthesis of (-)-pentazocine using optical resolution, see:
  • 33
    • 65549129882 scopus 로고    scopus 로고
    • For asymmetric synthesis of, -pentazocine, see
    • For asymmetric synthesis of (-)-pentazocine, see:
  • 37
    • 0022382945 scopus 로고
    • Asymmetric synthesis of (-)-metazocine (N-methyl derivative of (-)-pentazocine) has also been reported
    • Asymmetric synthesis of (-)-metazocine (N-methyl derivative of (-)-pentazocine) has also been reported. Meyers A.I., Dickman D.A., and Bailey T.R. J. Am. Chem. Soc. 107 (1985) 7974
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 7974
    • Meyers, A.I.1    Dickman, D.A.2    Bailey, T.R.3
  • 38
    • 48849117471 scopus 로고    scopus 로고
    • Very recently, the asymmetric synthesis of (-)-9-epi-pentazocine was also reported
    • Very recently, the asymmetric synthesis of (-)-9-epi-pentazocine was also reported. Yang X., Zhai H., and Li Z. Org. Lett. 10 (2008) 2457
    • (2008) Org. Lett. , vol.10 , pp. 2457
    • Yang, X.1    Zhai, H.2    Li, Z.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.