Solution-phase parallel synthesis of 115 homosilatecan analogues

Journal of Combinatorial Chemistry

Volumn 5, Issue 5, 2003, Pages 617-624

  Gabarda, Ana E ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CAMPTOTHECIN; IODOPYRIDONE; ISONITRILE DERIVATIVE; LACTONE;

ARTICLE; AUTOMATION; CHEMICAL REACTION; CHROMATOGRAPHY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

EID: 0141869937     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc030018g     Document Type: Article

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25. Ketone 8 and analogues also proved to be key intermediates in a new approach to the camptothecin DE pyridone - lactone intermediate. See: (a) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P. ; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908. (b) Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2923. (c) Yabu, K.; Masumoto, S.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. Heterocycles 2003, 59, 3695.
26. Ketone 8 and analogues also proved to be key intermediates in a new approach to the camptothecin DE pyridone - lactone intermediate. See: (a) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P. ; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908. (b) Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2923. (c) Yabu, K.; Masumoto, S.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. Heterocycles 2003, 59, 3695.
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29. Since hst{1,7} (DB-36) was synthesized within the first generation homosilatecans, this analogue was not included in the library synthesis. See Bom, D.; Curran, D. P.; Chavan, A. J.; Kruszewski, S.; Zimmer, S. G.; Fraley, K. A.; Burke, T. G. J. Med. Chem. 1999, 42, 3018. See also Bom, D. Ph.D. Thesis, University of Pittsburgh, 2000.
30. Since hst{1,7} (DB-36) was synthesized within the first generation homosilatecans, this analogue was not included in the library synthesis. See Bom, D.; Curran, D. P.; Chavan, A. J.; Kruszewski, S.; Zimmer, S. G.; Fraley, K. A.; Burke, T. G. J. Med. Chem. 1999, 42, 3018. See also Bom, D. Ph.D. Thesis, University of Pittsburgh, 2000.
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32. (b) See also de Frutos, O.; Curran, D. P. J. Comb. Chem. 2000, 2, 639.
33. -TMS derivatives hst{1,1-7} (Table 3) were purified by flash chromatography on silica gel. During the radical reactions of the TMS-propargylated iodopyridone 12{1}, the homosilatecan products were observed to precipitate out as they formed; thus, a difficult and low-yielding automated purification protocol was foreseen.
34. hst{11,8} was accidentally lost; thus, this member is not included in Table 6.
35. Reactions were followed by TLC analysis, and individual reaction times are given in the Supporting Information.
36. (a) Luo, Z. Y.; Zhang, Q. S.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766.
37. (b) Zhang, W.; Luo, Z.; Chen, C. H. T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443.