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Volumn 44, Issue 8, 2003, Pages 1591-1593

Enantioselective total synthesis of (-)-pseudophrynaminol through tandem olefination, isomerization and asymmetric Claisen rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

2 OXYINDOLIN 3 ONE; 3 INDOL 2 ONE; ALCOHOL DERIVATIVE; ALKALOID; CARBON; INDOLE DERIVATIVE; KETONE DERIVATIVE; PSEUDOPHRYAMINOL; PYRROLO[2,3 B]INDOLE; UNCLASSIFIED DRUG;

EID: 0037450477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00065-0     Document Type: Article
Times cited : (50)

References (39)
  • 13
    • 0012985348 scopus 로고    scopus 로고
    • For a review, see: Dayl, J. W.; Garraffo, H. M.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletiesr, S. W., Ed.; Pergamon Press: New York, 1999; Vol. 13, Chapter 1, pp. 1-161.
  • 33
    • 0012985124 scopus 로고    scopus 로고
    • note
    • Wittig olefination of 4 with methyl triphenylphosphoranylideneacetate in refluxing toluene for 9 h gave indolylidene acetate 15 in 86% yield. Reaction of 15 with DBU in toluene at 40°C for 38 h took place with successive isomerization and Claisen rearrangement to produce indolin-2-one 16 (60%) and its N-acetyl derivative (22%), respectively. In this case, allylic alcohol 3 with 93% ee was used as the starting material to obtain 16 with 92% ee.
  • 34
    • 0000217402 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford
    • Wipf P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp. 827-873;
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 827-873
    • Wipf, P.1
  • 37
    • 0013032950 scopus 로고    scopus 로고
    • note
    • The calculation was performed by using SPARTAN ver. 5.1.2 (pBP-DN**).
  • 38
    • 0012975802 scopus 로고    scopus 로고
    • note
    • 2: 258.1732; found: 258.1733.
  • 39
    • 0012934403 scopus 로고    scopus 로고
    • note
    • 3) (Ref. 12b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.