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Volumn 10, Issue 20, 2008, Pages 4693-4696

A chemoenzymatic total synthesis of the structure assigned to the alkaloid (+)-montabuphine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMARYLLIDACEAE ALKALOID; ENZYME; MONTABUPHINE; UNCLASSIFIED DRUG;

EID: 58149173852     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801815k     Document Type: Article
Times cited : (34)

References (37)
  • 1
    • 77957033352 scopus 로고
    • For reviews dealing with this class of alkaloid see: a, Brossi, A, Ed, Academic Press: San Diego
    • For reviews dealing with this class of alkaloid see: (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 30, p 251.
    • (1987) The Alkaloids , vol.30 , pp. 251
    • Martin, S.F.1
  • 2
    • 77956708370 scopus 로고    scopus 로고
    • Cordell, G. A, Ed, Academic Press: San Diego
    • (b) Hoshino, O. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 51, p 323.
    • (1998) The Alkaloids , vol.51 , pp. 323
    • Hoshino, O.1
  • 3
    • 0034141667 scopus 로고    scopus 로고
    • and previous reviews in the series
    • (c) Lewis, J. R. Nat. Prod. Rep. 20001757, and previous reviews in the series.
    • (2000) Nat. Prod. Rep , vol.17 , pp. 57
    • Lewis, J.R.1
  • 19
    • 61349190198 scopus 로고    scopus 로고
    • In assigning structure 3 to, -montabuphine, Codina et al. 4 did not explicitly define the stereochemistry at C4a but their commentary and the subsequent interpretations of others means that the illustrated R-configuration at this center is now widely assumed
    • 4 did not explicitly define the stereochemistry at C4a but their commentary and the subsequent interpretations of others means that the illustrated R-configuration at this center is now widely assumed.
  • 20
    • 0001846314 scopus 로고    scopus 로고
    • Compound 4 can be obtained from the Aldrich Chemical Co. (Catalogue Number 489492) or from Questor, Queen's University of Belfast, Northern Ireland (http://questor.qub.ac.uk/newsite/contact.htm). 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. Aldrichim. Acta 1999, 32, 35.
    • Compound 4 can be obtained from the Aldrich Chemical Co. (Catalogue Number 489492) or from Questor, Queen's University of Belfast, Northern Ireland (http://questor.qub.ac.uk/newsite/contact.htm). 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. Aldrichim. Acta 1999, 32, 35.
  • 25
    • 33744737931 scopus 로고    scopus 로고
    • For related examples of this type of radical reaction, see: a
    • For related examples of this type of radical reaction, see: (a) Stanislawski, P. C.; Willis, A. C.; Banwell, M. G. Org. Lett. 2006, 8, 2143.
    • (2006) Org. Lett , vol.8 , pp. 2143
    • Stanislawski, P.C.1    Willis, A.C.2    Banwell, M.G.3
  • 27
    • 4243241249 scopus 로고
    • For a very useful review of the Pictet, Spengler reaction, see
    • For a very useful review of the Pictet - Spengler reaction, see: Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
    • (1995) Chem. Rev , vol.95 , pp. 1797
    • Cox, E.D.1    Cook, J.M.2
  • 28
    • 42249099621 scopus 로고    scopus 로고
    • The regioselectivity observed in the conversion 8 → 9 has been rationlized elsewhere, see: Matveenko, M.; Banwell, M. G.; Willis, A. C. Tetrahedron 2008, 64, 4817.
    • The regioselectivity observed in the conversion 8 → 9 has been rationlized elsewhere, see: Matveenko, M.; Banwell, M. G.; Willis, A. C. Tetrahedron 2008, 64, 4817.
  • 32
    • 3042741556 scopus 로고
    • 7277. A very well-defined method for preparing this useful reagent has been reported
    • (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277. A very well-defined method for preparing this useful reagent has been reported:
    • (1991) J. Am. Chem. Soc , vol.113
    • Dess, D.B.1    Martin, J.C.2
  • 37
    • 61349116653 scopus 로고    scopus 로고
    • The structure of synthetically-derived 3 was confirmed by a single crystal X-ray analysis of its oxalate salt.
    • The structure of synthetically-derived 3 was confirmed by a single crystal X-ray analysis of its oxalate salt.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.