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Volumn 62, Issue 11, 1997, Pages 3592-3596

Total synthesis of desoxoprosophylline: Application of a lactam-derived enol triflate to natural product synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DESOXOPROSOPHYLLINE; UNCLASSIFIED DRUG;

EID: 0030961411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962347j     Document Type: Article
Times cited : (82)

References (28)
  • 1
    • 0027180141 scopus 로고
    • (a) Review: Ritter, K. Synthesis 1993, 735. (b) O'Neil, I. O.; Hamilton, K. M.; Miller, J. A.; Young, R. J. Synlett 1995, 151.
    • (1993) Synthesis , pp. 735
    • Ritter, K.1
  • 7
    • 0001673091 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 11
    • 0002437688 scopus 로고
    • Brossi, A., Ed; Academic Press: San Diego
    • (d) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed; Academic Press: San Diego, 1986; Vol. 26, p 89.
    • (1986) The Alkaloids , vol.26 , pp. 89
    • Strunz, G.M.1    Findlay, J.A.2
  • 23
    • 8544253485 scopus 로고    scopus 로고
    • note
    • The Lewis acidity of the TBDMSOTf occasionally caused partial elimination of EtOH from 13, affording an N-tosylenamide byproduct (ca. 5-15%). However, this was of little consequence as both 13 and the byproduct reacted with silane 15 in the next step.
  • 24
    • 0026759610 scopus 로고
    • and references therein
    • Åhman, J.; Somfai, P. Tetrahedron 1992, 48, 9537 and references therein.
    • (1992) Tetrahedron , vol.48 , pp. 9537
    • Åhman, J.1    Somfai, P.2
  • 26
    • 0000424631 scopus 로고
    • and references therein
    • For similar results with N-acyliminium ions, see: (a) Ludwig, C.; Wistrand, L.-G. Acta Chem. Scand. 1994, 48, 367 and references therein. (b) Shono, T.; Matsumura, Y.; Onomura, O.; Sato, M. J. Org. Chem. 1988, 53, 4118.
    • (1994) Acta Chem. Scand. , vol.48 , pp. 367
    • Ludwig, C.1    Wistrand, L.-G.2
  • 27
    • 0023715081 scopus 로고
    • For similar results with N-acyliminium ions, see: (a) Ludwig, C.; Wistrand, L.-G. Acta Chem. Scand. 1994, 48, 367 and references therein. (b) Shono, T.; Matsumura, Y.; Onomura, O.; Sato, M. J. Org. Chem. 1988, 53, 4118.
    • (1988) J. Org. Chem. , vol.53 , pp. 4118
    • Shono, T.1    Matsumura, Y.2    Onomura, O.3    Sato, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.