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Volumn 71, Issue 8, 2008, Pages 1431-1440

Enantiospecific synthesis of (+)-alstonisine via a stereospecific osmylation process

Author keywords

[No Author keywords available]

Indexed keywords

ALSTONISINE; INDOLE; INDOLE ALKALOID; INDOLE DERIVATIVE; NITROGEN DERIVATIVE; OSMIUM TETRAOXIDE; OXINDOLE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 51849150742     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800269k     Document Type: Article
Times cited : (67)

References (69)
  • 1
    • 0037191618 scopus 로고    scopus 로고
    • A preliminary account of part of this work has been reported, see
    • A preliminary account of part of this work has been reported, see: Wearing, X. Z.; Cook, J. M. Org. Lett. 2002, 4, 4237.
    • (2002) Org. Lett , vol.4 , pp. 4237
    • Wearing, X.Z.1    Cook, J.M.2
  • 15
    • 51849166217 scopus 로고    scopus 로고
    • Japanese Patent 03284 622: Chem. Abstr. 1991, 117 10, 97324
    • Japanese Patent 03284 622: Sakai, S.; Sugita, M.; Katsuyama, K.; Honjo, E. Chem. Abstr. 1991, 117 (10), 97324.
    • Sakai, S.1    Sugita, M.2    Katsuyama, K.3    Honjo, E.4
  • 64
    • 51849113974 scopus 로고    scopus 로고
    • b-Bn tetracyclic series 14.
    • b-Bn tetracyclic series 14.
  • 65
    • 0042366277 scopus 로고    scopus 로고
    • In earlier work, a single-crystal X-ray analysis of an N b-benzyhetracyclic derivative also indicated that the benzyl group rested in the axial position of the D ring in the crystal: Zhang, L. H, Trudell, M. L, Hollinsnead, S. P, Cook, J. M. J. Am. Chem. Soc. 1989, 111, 8263. In solution this has been supported by analysis of NOE studies. The concomitant complexation of osmium at the equatorial position (with respect to ring D) of indole 51 facilitated intramolecular attack of the osmium reagent to furnish osmate ester 29 (Scheme 4) upon heating at reflux. If complexation occurred at the axial position (with respect to the D ring) of indole 52 to give a complex, the intramolecular delivery of the osmium reagent to the 2,3-indole double bond would be unlikely; see ref 17, Chemical Equation Presented
    • b-benzyhetracyclic derivative also indicated that the benzyl group rested in the axial position of the D ring in the crystal: Zhang, L. H.; Trudell, M. L.; Hollinsnead, S. P.; Cook, J. M. J. Am. Chem. Soc. 1989, 111, 8263. In solution this has been supported by analysis of NOE studies. The concomitant complexation of osmium at the equatorial position (with respect to ring D) of indole 51 facilitated intramolecular attack of the osmium reagent to furnish osmate ester 29 (Scheme 4) upon heating at reflux. If complexation occurred at the axial position (with respect to the D ring) of indole 52 to give a complex, the intramolecular delivery of the osmium reagent to the 2,3-indole double bond would be unlikely; see ref 17. (Chemical Equation Presented)


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