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Volumn 47, Issue 1, 2008, Pages 205-208

On the origin of the haouamine alkaloids

Author keywords

Alkaloids; Biosynthesis; Cascade reactions; Natural products; Total synthesis

Indexed keywords

ALKALOIDS; CASCADE REACTIONS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 37549003646     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704576     Document Type: Article
Times cited : (47)

References (35)
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    • Studies toward the haouamines: a N. D. Smith, J. Hayashida, V. H. Rawal, Org. Lett. 2005, 7, 4309-4312;
    • Studies toward the haouamines: a) N. D. Smith, J. Hayashida, V. H. Rawal, Org. Lett. 2005, 7, 4309-4312;
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    • 23844504774 scopus 로고    scopus 로고
    • Heating an ammonia saturated solution of phenylacetaldehyde in ethanol to 235°C at 1150 psi for 6 h yields 13% 3,5-diphenylpyridine: E. L. Eliel, R. T. McBride, S. Kaufmann, J. Am. Chem. Soc. 1953, 75, 4291-4296;
    • a) Heating an ammonia saturated solution of phenylacetaldehyde in ethanol to 235°C at 1150 psi for 6 h yields 13% 3,5-diphenylpyridine: E. L. Eliel, R. T. McBride, S. Kaufmann, J. Am. Chem. Soc. 1953, 75, 4291-4296;
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    • reduction of m-methoxyphenylacetamide with lithium aluminum hydride (LAH) yields 17% 3,5-bis(m-methoxyphenyl)pyridine: D. R. Eckroth, Chem. Ind. 1967, 920-921.
    • b) reduction of m-methoxyphenylacetamide with lithium aluminum hydride (LAH) yields 17% 3,5-bis(m-methoxyphenyl)pyridine: D. R. Eckroth, Chem. Ind. 1967, 920-921.
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    • Selected examples: A. Kumar, R. A. Rhodes, J. Spychala, W. D. Wilson, D. W. Boykin, R. R. Tidwell, C. C. Dykstra, J. E. Hall, S. K. Jones, R. F. Schinazi, Eur. J. Med. Chem. 1995, 30, 99-106;
    • Selected examples: A. Kumar, R. A. Rhodes, J. Spychala, W. D. Wilson, D. W. Boykin, R. R. Tidwell, C. C. Dykstra, J. E. Hall, S. K. Jones, R. F. Schinazi, Eur. J. Med. Chem. 1995, 30, 99-106;
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    • Conducting this reaction in an oxygen-saturated environment leads to a rate enhancement as determined by 1H NMR spectroscopy; further mechanistic studies will be reported in a full account of this work;
    • 1H NMR spectroscopy; further mechanistic studies will be reported in a full account of this work;
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    • for examples of metal-catalyzed oxidative dealkylation of dihydropyridines, see
    • b) for examples of metal-catalyzed oxidative dealkylation of dihydropyridines, see: R. W. Saalfrank, S. Reihs, M. Hug, Tetrahedron Lett. 1993, 34, 6033-6036;
    • (1993) Tetrahedron Lett , vol.34 , pp. 6033-6036
    • Saalfrank, R.W.1    Reihs, S.2    Hug, M.3
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    • 37549002205 scopus 로고    scopus 로고
    • Although the spectra of 23 matches those reported by the authors for 22, it is clearly 23 based on spectroscopic measurements see Supporting Information for further details
    • Although the spectra of 23 matches those reported by the authors for 22, it is clearly 23 based on spectroscopic measurements (see Supporting Information for further details).
  • 20
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    • For a review, see:, Eds, B. M. Trost, I. Fleming, Pergamon, Oxford
    • For a review, see: I. E. Markó in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 913-974.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 913-974
    • Markó, I.E.1
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    • For a beautiful application in total synthesis, see
    • For a beautiful application in total synthesis, see: B. B. Snider, B. J. Neubert, Org. Lett. 2005, 7, 2715-2718.
    • (2005) Org. Lett , vol.7 , pp. 2715-2718
    • Snider, B.B.1    Neubert, B.J.2
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    • Angew. Chem. Int. Ed. 1998, 37, 388-401;
    • (1998) Chem. Int. Ed , vol.37 , pp. 388-401
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    • See Supporting Information for synthetic details
    • See Supporting Information for synthetic details.
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    • Angew. Chem. Int. Ed. 2007, 46, 3252-3254.
    • (2007) Chem. Int. Ed , vol.46 , pp. 3252-3254
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    • 37549060066 scopus 로고    scopus 로고
    • Deuterium labeling studies strongly suggest an allyl [1,2]-shift as implied in 34 assuming a chelated transition state 32:. (Chemical Equation Presented)
    • Deuterium labeling studies strongly suggest an allyl [1,2]-shift as implied in 34 assuming a chelated transition state 32:. (Chemical Equation Presented)
  • 34
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    • Biological meta-hydroxylation of L-phenylalanine is known: J. H. Tong, A. D'Iorio, N. L. Benoiton, Biochem. Biophys. Res. Commun. 1971, 44, 229-236.
    • Biological meta-hydroxylation of L-phenylalanine is known: J. H. Tong, A. D'Iorio, N. L. Benoiton, Biochem. Biophys. Res. Commun. 1971, 44, 229-236.
  • 35
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    • CCDC-664780, CCDC-664678, CCDC-664679, CCDC-664680, CCDC-664681, and CCDC-664682 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • CCDC-664780, CCDC-664678, CCDC-664679, CCDC-664680, CCDC-664681, and CCDC-664682 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.