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Volumn 63, Issue 41, 2007, Pages 10337-10344

Intramolecular Diels-Alder reactions of oxazole-olefins: synthesis of the Rauwolfia alkaloids suaveoline and norsuaveoline

Author keywords

Amino acids; Diels Alder reaction; Indole alkaloids; Oxazoles

Indexed keywords

ALKENE; NORSUAVEOLINE; OXAZOLE; RAUWOLFIA ALKALOID; SUAVEOLINE; UNCLASSIFIED DRUG;

EID: 34548200790     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.070     Document Type: Article
Times cited : (32)

References (66)
  • 1
    • 9444246242 scopus 로고    scopus 로고
    • For a recent review on the oxazole Diels-Alder reactions, see:. Palmer D.C. (Ed), John Wiley and Sons, Hoboken, NJ pp 417-472, Part A
    • For a recent review on the oxazole Diels-Alder reactions, see:. Levin J.I., and Laakso L.M. In: Palmer D.C. (Ed). The Chemistry of Heterocyclic Compounds Vol. 60 (2003), John Wiley and Sons, Hoboken, NJ pp 417-472, Part A
    • (2003) The Chemistry of Heterocyclic Compounds , vol.60
    • Levin, J.I.1    Laakso, L.M.2
  • 3
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    • Chem. Abstr. 52 (1958) 6345a
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    • Chem. Abstr. 53 (1959) 21940d
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  • 8
    • 0000333624 scopus 로고
    • For other intramolecular oxazole-olefin Diels-Alder reactions, see: (a)
    • For other intramolecular oxazole-olefin Diels-Alder reactions, see: (a). Shimada S., and Tojo T. Chem. Pharm. Bull. 31 (1983) 4247-4258
    • (1983) Chem. Pharm. Bull. , vol.31 , pp. 4247-4258
    • Shimada, S.1    Tojo, T.2
  • 21
    • 4143076856 scopus 로고    scopus 로고
    • A preliminary account of this work has been published:
    • A preliminary account of this work has been published:. Ohba M., Natsutani I., and Sakuma T. Tetrahedron Lett. 45 (2004) 6471-6474
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6471-6474
    • Ohba, M.1    Natsutani, I.2    Sakuma, T.3
  • 56
    • 34548207662 scopus 로고    scopus 로고
    • b-benzyltryptophan methyl ester with methyl propiolate is known to furnish predominantly the trans-tetrahydro-β-carboline derivative:
  • 62
    • 34548243635 scopus 로고    scopus 로고
    • note
    • Owing to the restricted rotation of the carbamate group, one of two methylene protons adjacent to the ester group showed two signals. The signals based on another proton appeared at δ 2.60 and 2.71.
  • 64
    • 34548216751 scopus 로고    scopus 로고
    • note
    • Such a disagreement may be due to traces of impurities: a private communication from Prof. J. M. Cook (University of Wisconsin-Milwaukee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.