메뉴 건너뛰기




Volumn 65, Issue 15, 2000, Pages 4671-4678

The [4 + 2] addition of singlet oxygen to thebaine: New access to highly functionalized morphine derivatives via opioid endoperoxides

Author keywords

[No Author keywords available]

Indexed keywords

14 HYDROXYCODEINONE; BENZOFURAN DERIVATIVE; BUPRENORPHINE; ENDOPEROXIDE; ETORPHINE; METHADONE; MORPHINE DERIVATIVE; NALOXONE; NARCOTIC ANALGESIC AGENT; OPIATE AGONIST; OXYCODONE; OXYMORPHONE; PREFIN; THEBAINE; TRAMADOL; UNCLASSIFIED DRUG;

EID: 0343526760     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000288a     Document Type: Article
Times cited : (23)

References (32)
  • 3
  • 5
    • 1842358322 scopus 로고
    • Manske, R. H. F., Holmes, H. L., Eds.; Academic Press: New York, and references therein
    • (e) Bentley, K. W. The Alkaloids, Chemistry and Pharmacology; Manske, R. H. F., Holmes, H. L., Eds.; Academic Press: New York, 1971; Vol. XIII, p 75, and references therein.
    • (1971) The Alkaloids, Chemistry and Pharmacology , vol.13 , pp. 75
    • Bentley, K.W.1
  • 7
    • 0011283625 scopus 로고
    • Discovery of Buprenorphine, a Potent Antagonist Analgesic
    • Roberts, S. M., Price, B. J., Eds.; Academic Press: London, and references therein
    • Lewis, J. W. Discovery of Buprenorphine, a Potent Antagonist Analgesic. In Medicinal Chemistry. The Role of Organic Chemistry in Drug Research; Roberts, S. M., Price, B. J., Eds.; Academic Press: London, 1985; p 119, and references therein.
    • (1985) Medicinal Chemistry. the Role of Organic Chemistry in Drug Research , pp. 119
    • Lewis, J.W.1
  • 15
    • 0028108831 scopus 로고
    • Three patents have been issued: Riguera, R.; Quiñoá, E.; López, D., Patents P9602716, P9602717 and P9602718, 1996
    • López, D.; Quiñoá, E.; Riguera, R. Tetrahedron Lett. 1994, 35, 5727. Three patents have been issued: Riguera, R.; Quiñoá, E.; López, D., Patents P9602716, P9602717 and P9602718, 1996.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5727
    • López, D.1    Quiñoá, E.2    Riguera, R.3
  • 16
    • 0002868580 scopus 로고
    • Endoperoxides
    • Ando, W., Ed.; Wiley: New York
    • For a general reference on peroxides see: Clennan, E. L.; Foot, C. S. Endoperoxides. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992. See also: Akaeshi, T.; Ando, W. Peroxides from Photosentitized Oxidation of Hetero Atom Compounds. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992.
    • (1992) Organic Peroxides
    • Clennan, E.L.1    Foot, C.S.2
  • 17
    • 0343123173 scopus 로고
    • Peroxides from Photosentitized Oxidation of Hetero Atom Compounds
    • Ando, W., Ed.; Wiley: New York
    • For a general reference on peroxides see: Clennan, E. L.; Foot, C. S. Endoperoxides. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992. See also: Akaeshi, T.; Ando, W. Peroxides from Photosentitized Oxidation of Hetero Atom Compounds. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992.
    • (1992) Organic Peroxides
    • Akaeshi, T.1    Ando, W.2
  • 22
    • 0343995274 scopus 로고    scopus 로고
    • note
    • The stereoselectivity of Diels-Alder reactions of thebaine is known to produce exclusively the adducts formed at the less hindered face of the diene (see ref 1e). The transformation of 32 into 35 (a known compound), confirmed the assigned stereochemistry of 32.
  • 23
    • 0343123172 scopus 로고    scopus 로고
    • note
    • The importance of the presence of free amino and hydroxy groups in opioids and their interactions with the opiate receptors is well documented, with numerous pharmacologically active derivatives incorporating such groups within their structures. See ref 1.
  • 24
    • 0342688884 scopus 로고    scopus 로고
    • Reference 1c, pp 139-213
    • Reference 1c, pp 139-213.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.