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Volumn 61, Issue 38, 2005, Pages 9147-9156

A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine

Author keywords

Enamines; Eseroline; Physostigmine; Sigmatropic rearrangements

Indexed keywords

1 (2' METHOXYCARBONYL N METHYLVINYLAMINO)SKATOLE; DESOXYESEROLINE; ENAMINE; HEXAHYDROPYRROLO[2,3 B]INDOLE; INDOLE DERIVATIVE; PHYSOSTIGMINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 23944510845     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.030     Document Type: Article
Times cited : (22)

References (59)
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    • A. Brossi Academic New York
    • For reviews of Calabar bean alkaloids, see: (a) S. Takano, and K. Ogasawara A. Brossi The Alkaloids Vol. 36 1989 Academic New York 225 251
    • (1989) The Alkaloids , vol.36 , pp. 225-251
    • Takano, S.1    Ogasawara, K.2
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    • (d) Roquefortine: P.M. Scott, M.-A. Merrien, and J. Polonsky Experientia 32 1976 140 142 These are a few examples of natural products that are characterised by the presence of diketopiperazine ring built on a hexahydropyrrolo[2,3-b]indole nucleus
    • (1976) Experientia , vol.32 , pp. 140-142
    • Scott, P.M.1    Merrien, M.-A.2    Polonsky, J.3
  • 11
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    • For recent reviews on pharmacological properties, see: (a) A. Brossi J. Med. Chem. 33 1990 2311 2319
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    • Brossi, A.1
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    • note
    • 24 For more recent examples see Refs. 9l and v.
  • 41
    • 0001726634 scopus 로고
    • For an elegant construction of hexahydropyrrolo[2,3-b]indole nucleus from a o-amino styrene derivative with simultaneous formation of rings B and C, involving a formamidine ylide cycloaddition, see: (a) R. Smith, and T. Livinghouse J. Org. Chem. 48 1983 1554 1555
    • (1983) J. Org. Chem. , vol.48 , pp. 1554-1555
    • Smith, R.1    Livinghouse, T.2
  • 51
    • 0000431085 scopus 로고
    • These compounds, unlike Barton esters, are characterised by greater thermal stability and longer shelf lives, see: M. Hasabe, and T. Tsuchiya Tetrahedron Lett. 28 1987 6207 6210
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6207-6210
    • Hasabe, M.1    Tsuchiya, T.2
  • 58
    • 33645409388 scopus 로고
    • Aldrich Chemical Company: Milwaukee
    • The Aldrich Library of FT-IR Spectra; Aldrich Chemical Company: Milwaukee, 1985; 3, 1104A.
    • (1985) The Aldrich Library of FT-IR Spectra , vol.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.