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Volumn 11, Issue 15, 2009, Pages 3506-3509

Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques

Author keywords

[No Author keywords available]

Indexed keywords

AMARYLLIDACEAE ALKALOID; BROMOBENZENE; ENZYME; LYCORINE; NITROBENZOIC ACID DERIVATIVE; PHENANTHRIDINE DERIVATIVE;

EID: 68149142567     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901364n     Document Type: Article
Times cited : (31)

References (46)
  • 1
    • 77957083775 scopus 로고
    • Manské, R. H. F, Holmes, H. L, Eds, Academic Press: New York
    • (a) Cook, J. W.; Loudon, J. D. In The Alkaloids; Manské, R. H. F., Holmes, H. L., Eds.; Academic Press: New York, 1952; Vol. 2, p 331.
    • (1952) The Alkaloids , vol.2 , pp. 331
    • Cook, J.W.1    Loudon, J.D.2
  • 10
    • 0000427207 scopus 로고    scopus 로고
    • For a review of the chemistry and biological effects of lycorine and related Amaryllidaceae alkaloids, see: Ghosal, S.; Saini, K. S.; Razdan, S. Phytochemistry 1985, 24, 2141.
    • For a review of the chemistry and biological effects of lycorine and related Amaryllidaceae alkaloids, see: Ghosal, S.; Saini, K. S.; Razdan, S. Phytochemistry 1985, 24, 2141.
  • 11
    • 68149088934 scopus 로고    scopus 로고
    • For more recent publications reporting on the biological properties of lycorine and its derivatives see: (a) Dickneite, G, Schorlemmer, H. U, Sedlaček, H. H. Ger. Offen. DE 3426109, Jan 23, 1986;
    • For more recent publications reporting on the biological properties of lycorine and its derivatives see: (a) Dickneite, G.; Schorlemmer, H. U.; Sedlaček, H. H. Ger. Offen. DE 3426109, Jan 23, 1986;
  • 12
    • 68149176246 scopus 로고
    • Chem. Abstr. 1986, 104, 161979.
    • (1986) Chem. Abstr , vol.104 , pp. 161979
  • 15
    • 33947480906 scopus 로고    scopus 로고
    • Synthetic approaches: (a) Hill, R. K.; Joule, J. A.; Loeffler, L. J. J. Am. Chem. Soc. 1962, 84, 4951.
    • Synthetic approaches: (a) Hill, R. K.; Joule, J. A.; Loeffler, L. J. J. Am. Chem. Soc. 1962, 84, 4951.
  • 24
    • 37049124978 scopus 로고    scopus 로고
    • Total syntheses or formal total syntheses of (±)-lycorine: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933.
    • Total syntheses or formal total syntheses of (±)-lycorine: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933.
  • 25
    • 0017892113 scopus 로고    scopus 로고
    • M0ller, O.; Steinberg, E.-M.; Torsseil, K. Acta Chem. Scand. B 1978, 32, 98.
    • (b) M0ller, O.; Steinberg, E.-M.; Torsseil, K. Acta Chem. Scand. B 1978, 32, 98.
  • 30
    • 0030037716 scopus 로고    scopus 로고
    • Total synthesis of (+)- or (-)-lycorine: (a) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210. [(+)-lycorine].
    • Total synthesis of (+)- or (-)-lycorine: (a) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210. [(+)-lycorine].
  • 32
    • 0001846314 scopus 로고    scopus 로고
    • Compound 3 can be obtained from the Aldrich Chemical Co. (Catalogue Number 489492) or from Questor, Queen's University of Belfast, Northern Ireland. Questor Centre Contact Page: http://questor.qub.ac.uk/ newsite/contact.htm (accessed July 2, 2009). For reviews on methods for generating cis-1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see: (a) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, 32, 35.
    • Compound 3 can be obtained from the Aldrich Chemical Co. (Catalogue Number 489492) or from Questor, Queen's University of Belfast, Northern Ireland. Questor Centre Contact Page: http://questor.qub.ac.uk/ newsite/contact.htm (accessed July 2, 2009). For reviews on methods for generating cis-1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see: (a) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, 32, 35.
  • 41
    • 0034554740 scopus 로고    scopus 로고
    • In keeping with expectations (Chaumeil, H.; Signorella, S.; Le Drian, C Tetrahedron 2000, 56, 9655) the 2,2-dimethyl-l,3- propanediol derived boronate 9, which was readily prepared by the methods defined in the Supporting Information, proved a more effective coupling partner than its pinacol-derived equivalent
    • In keeping with expectations (Chaumeil, H.; Signorella, S.; Le Drian, C Tetrahedron 2000, 56, 9655) the 2,2-dimethyl-l,3- propanediol derived boronate 9, which was readily prepared by the methods defined in the Supporting Information, proved a more effective coupling partner than its pinacol-derived equivalent
  • 44
    • 49149145492 scopus 로고
    • For a review of this type of process, see
    • For a review of this type of process, see:Magid, R. M. Tetrahedron 1980, 36, 1901.
    • (1980) Tetrahedron , vol.36 , pp. 1901
    • Magid, R.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.