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Volumn 45, Issue 34, 2004, Pages 6471-6474

Total synthesis of suaveoline and norsuaveoline via intramolecular oxazole-olefin Diels-Alder reaction

Author keywords

Alkaloids; Amino acids and derivatives; Diels Alder reactions; Indoles; Oxazoles

Indexed keywords

ALKENE; ESTER DERIVATIVE; INDOLE ALKALOID; METHYL GROUP; NORSUAVEOLINE; OXAZOLE; RAUWOLFIA ALKALOID; SUAVEOLINE; TRYPTOPHAN; UNCLASSIFIED DRUG;

EID: 4143076856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.108     Document Type: Article
Times cited : (45)

References (40)
  • 3
    • 0017386125 scopus 로고
    • Suaveoline (1) has been found in other species of Rauwolfia, see: M.M. Iwu, and W.E. Court Planta Med. 32 1977 88 99
    • (1977) Planta Med. , vol.32 , pp. 88-99
    • Iwu, M.M.1    Court, W.E.2
  • 29
    • 0020563556 scopus 로고
    • For the intramolecular oxazole-olefin Diels-Alder reaction, see: J.I. Levin, and S.M. Weinreb J. Am. Chem. Soc. 105 1983 1397 1398
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1397-1398
    • Levin, J.I.1    Weinreb, S.M.2
  • 33
    • 4143056434 scopus 로고    scopus 로고
    • note
    • Recrystallized from AcOEt-hexane
  • 36
    • 4143146918 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy using a chiral shift reagent
  • 37
    • 4143050789 scopus 로고    scopus 로고
    • note
    • Two methylene protons adjacent to the 1-position in 15 showed two sets of signals, respectively, owing to the restricted rotation of the carbamate group
  • 40
    • 4143070874 scopus 로고    scopus 로고
    • note
    • Such 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.