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Volumn 8, Issue 1, 2006, Pages 83-86

Co2(CO)8-catalyzed intramolecular hetero-Pauson-Khand reaction of alkynecarbodiimide: Synthesis of (±)-physostigmine

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CYANAMIDE; PHYSOSTIGMINE;

EID: 30944460158     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052562z     Document Type: Article
Times cited : (106)

References (60)
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    • (d) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037-1064
    • Schore, N.E.1
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    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York
    • (e) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, pp 703-739.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 703-739
    • Schore, N.E.1
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    • (g) Jeong, N. In Transition Metals in Organic Synthesis; Beller, H., Bolm, C., Eds; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 560-577.
    • (1998) Transition Metals in Organic Synthesis , vol.1 , pp. 560-577
    • Jeong, N.1
  • 24
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    • The thermal transformation of the N-[2-(1-alkynyl)phenyl]-N′- phenylcarbodiimides into the 6H-indolo[2,3-b]qinolines via the biradical intermediates and its related reactions were reported; see: (a) Schmittel, M.; Steffen, J.-P.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. 1998, 37, 2371-2373.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2371-2373
    • Schmittel, M.1    Steffen, J.-P.2    Engels, B.3    Lennartz, C.4    Hanrath, M.5
  • 45
    • 30944469889 scopus 로고    scopus 로고
    • note
    • The formation of the urea derivative 4 as a byproduct could tentatively be interpreted by hydrolysis with a small amount of water inevitably present in the reaction medium.
  • 55
    • 30944434070 scopus 로고    scopus 로고
    • note
    • 8 (20 mol %) was used.
  • 56
    • 30944455749 scopus 로고    scopus 로고
    • note
    • 6 (1.2 equiv) and DMSO (10 equiv) afforded the desired 9 in 78% yield along with the urea 7 in 8% yield.
  • 57
    • 30944436531 scopus 로고    scopus 로고
    • note
    • Coumpound 8 was prepared from 3j via 7.
  • 58
    • 30944448488 scopus 로고    scopus 로고
    • note
    • 8a) would be susceptible to the hydride reduction, followed by N-methylation to produce 10.
  • 59
    • 30944455137 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 10 was determined by an NOE experiment.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.