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Volumn 73, Issue 19, 2008, Pages 7779-7782

Short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B and a formal synthesis of nectrisine

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINO ACIDS; CHEMICAL REACTIONS; ORGANIC COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

EID: 53049084856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8012989     Document Type: Article
Times cited : (38)

References (79)
  • 44
    • 0043157614 scopus 로고    scopus 로고
    • Analogues and surrogates of nectrisine with a similar pharmacological profile have also been prepared. See: (a) Tschamber, T, Gessier, F, Neuburger, M, Gurcha, S. S, Besra, G. S, Streith, J, Chem. 2003, 2792-2798
    • Analogues and surrogates of nectrisine with a similar pharmacological profile have also been prepared. See: (a) Tschamber, T.; Gessier, F.; Neuburger, M.; Gurcha, S. S.; Besra, G. S.; Streith, J. Eur. J. Org. Chem. 2003, 2792-2798.
  • 50
    • 0032427086 scopus 로고    scopus 로고
    • Prepared from D-serine according to: Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709.
    • Prepared from D-serine according to: Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709.
  • 52
    • 0027499972 scopus 로고    scopus 로고
    • Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2956. Our modification consisted in carrying out the dihydroxylation by means of the Sharpless asymmetric procedure. In this way, the overall yield of 5 from Garner's (R)-aldehyde was improved from ca. 50 to 83% (see Experimental Section).
    • Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2956. Our modification consisted in carrying out the dihydroxylation by means of the Sharpless asymmetric procedure. In this way, the overall yield of 5 from Garner's (R)-aldehyde was improved from ca. 50 to 83% (see Experimental Section).
  • 53
    • 0012063703 scopus 로고    scopus 로고
    • For examples of O-benzylation with this method, see: (a) Mislow, K, O'Brien, R. E, Schaefer, H. J. Am. Chem. Soc. 1962, 84, 1940-1944
    • For examples of O-benzylation with this method, see: (a) Mislow, K.; O'Brien, R. E.; Schaefer, H. J. Am. Chem. Soc. 1962, 84, 1940-1944.
  • 58
    • 0000758675 scopus 로고    scopus 로고
    • For reviews on Weinreb amides, see: a
    • For reviews on Weinreb amides, see: (a) Mentzel, M.; Hoffmann, H. M. R. J. Prakt. Chem. 1997, 339, 517-524.
    • (1997) J. Prakt. Chem , vol.339 , pp. 517-524
    • Mentzel, M.1    Hoffmann, H.M.R.2
  • 61
    • 0029084414 scopus 로고    scopus 로고
    • The conditions used for the preparation of Weinreb amide 8 were taken from: Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
    • The conditions used for the preparation of Weinreb amide 8 were taken from: Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
  • 63
    • 53049100530 scopus 로고    scopus 로고
    • The stereochemical course of the reduction of 9 was assumed to be as depicted in Scheme 2 upon reliance on the results in the reduction of a ketone closely related to 9 (with an alkyl residue instead of the aryl group), where the configuration of the alcohol was secured by means of X-ray diffraction (unpublished results).
    • The stereochemical course of the reduction of 9 was assumed to be as depicted in Scheme 2 upon reliance on the results in the reduction of a ketone closely related to 9 (with an alkyl residue instead of the aryl group), where the configuration of the alcohol was secured by means of X-ray diffraction (unpublished results).
  • 65
    • 0033942849 scopus 로고    scopus 로고
    • For some recent examples of pyrrolidine ring closure via intramolecular nucleophilic displacement, see for example: a
    • For some recent examples of pyrrolidine ring closure via intramolecular nucleophilic displacement, see for example: (a) Yoda, H.; Asai, F.; Takabe, K. Synlett 2000, 1001-1003.
    • (2000) Synlett , pp. 1001-1003
    • Yoda, H.1    Asai, F.2    Takabe, K.3
  • 68
    • 53049102983 scopus 로고    scopus 로고
    • This idea was suggested by the fact that acidic treatment of alcohol 10 under similar conditions as 4 (TFA, 1 h, 0°C) also gave a 2:1 mixture of pyrrolidines 11, together with extensive decomposition
    • This idea was suggested by the fact that acidic treatment of alcohol 10 under similar conditions as 4 (TFA, 1 h, 0°C) also gave a 2:1 mixture of pyrrolidines 11, together with extensive decomposition.
  • 74
    • 53049109407 scopus 로고    scopus 로고
    • Mixtures of 2 and 13 (5-epi-radicamine B) of variable composition were obtained, with the undesired 13 being always the major compound.
    • Mixtures of 2 and 13 (5-epi-radicamine B) of variable composition were obtained, with the undesired 13 being always the major compound.
  • 75
    • 34249110615 scopus 로고    scopus 로고
    • For a synthesis of 13, see: Zhou, X.; Liu, W.-J.; Ye, J.-L.; Huang, P.-Q. Tetrahedron 2007, 63, 6346-6357.
    • For a synthesis of 13, see: Zhou, X.; Liu, W.-J.; Ye, J.-L.; Huang, P.-Q. Tetrahedron 2007, 63, 6346-6357.
  • 77
    • 44349092998 scopus 로고    scopus 로고
    • For a similar situation, see for example
    • For a similar situation, see for example: Yu, D.-S.; Xu, W.-X.; Liu, L.-X.; Huang, P.-Q. Synlett 2008, 1189-1192.
    • (2008) Synlett , pp. 1189-1192
    • Yu, D.-S.1    Xu, W.-X.2    Liu, L.-X.3    Huang, P.-Q.4
  • 79
    • 53049106808 scopus 로고    scopus 로고
    • The syntheses reported in ref 7g, 9 involve reaction sequences of 9-11 steps from D-xylose, L-xylose, or L-arabinose as the starting materials. Overall yields were in the range from 8 to 17%.
    • The syntheses reported in ref 7g, 9 involve reaction sequences of 9-11 steps from D-xylose, L-xylose, or L-arabinose as the starting materials. Overall yields were in the range from 8 to 17%.


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