Cascade 4+1 radical annulations of 2,6-disubstituted phenyl isonitriles with N-propargyl-6-iodopyridones: Scope, mechanism and regioselective synthesis of 7,9-disubstituted camptothecin analogs

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1299-1302

  Du, Wu ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Camptothecin; Cascade radical annulation; Isonitrile; Mappicine; Quinoline

Indexed keywords

7 TRIMETHYLSILYL 9 ISOPROPYLCAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; ISONITRILE DERIVATIVE; N PROPARGYL 6 IODOPYRIDONE DERIVATIVE; PHENYLISONITRILE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0037765594     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40327     Document Type: Article

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26. Fragmentation reactions of cyclohexadienyl-like radicals with rearomatization are well precedented. See, for example: (a) Binmore, G.; Walton, J. C.; Cardellini, L. J. Chem. Soc., Chem. Commun. 1995, 27. (b) Jackson, L.; Walton, J. C. Tetrahedron Lett. 1999, 40, 7019. (c) Jackson, L. V.; Walton, J. C. Chem. Commun. 2000, 2327.
27. Fragmentation reactions of cyclohexadienyl-like radicals with rearomatization are well precedented. See, for example: (a) Binmore, G.; Walton, J. C.; Cardellini, L. J. Chem. Soc., Chem. Commun. 1995, 27. (b) Jackson, L.; Walton, J. C. Tetrahedron Lett. 1999, 40, 7019. (c) Jackson, L. V.; Walton, J. C. Chem. Commun. 2000, 2327.
28. Fragmentation reactions of cyclohexadienyl-like radicals with rearomatization are well precedented. See, for example: (a) Binmore, G.; Walton, J. C.; Cardellini, L. J. Chem. Soc., Chem. Commun. 1995, 27. (b) Jackson, L.; Walton, J. C. Tetrahedron Lett. 1999, 40, 7019. (c) Jackson, L. V.; Walton, J. C. Chem. Commun. 2000, 2327.
29. Supporting Information Available: A print or pdf file of the characterization data for the compounds in this paper can be obtained on request from DPC.