Total synthesis of a biotinylated derivative of phorboxazole A via Sonogashira coupling

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 13, 2003, Pages 2127-2130

  Hansen, T Matthew ^a,b   Engler, Mary M ^a   Forsyth, Craig J ^a  

^a University of Minnesota   (United States)

^b ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN; CARBON; PALLADIUM; PHORBOXAZOLE A; PYRROLE DERIVATIVE;

ARTICLE; BIOTINYLATION; COVALENT BOND; CYTOSTASIS; DEPROTECTION REACTION; DERIVATIZATION; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0037534109     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00355-X     Document Type: Article

References (18)

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9. (a) Portions of this work are described in the PhD. Thesis of T. M. Hansen, University of Minnesota, 2002.
10. (b) Hansen, T. M.; Engler, M. M.; Forsyth, C. J. Abstracts of Papers, 222nd National Meeting of the American Chemical Society: Chicago, IL, Aug 2001; American Chemical Society: Washington D.C., 2001, ORGN 199.
11. (c) The biological activity of 2 has been reported: Uckun F.M., Forsyth C.J. Bioorg. Med. Chem. Lett. 11:2001;1181. and references cited within.
12. Compounds 2 and 7 were first synthesized as described in: C. S. Lee, PhD. Thesis, University of Minnesota, 1999. An enhanced synthetic route is described in ref 3a, and will be detailed further in due course.
13. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467.
14. (a) Fujii, K.; Hatano, K.; Nakamura, K.; Umeyama, H. Jpn. Kokai Tokkyo Koho, 2001, JP 2001064238.
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16. (c) Pou, T. E.; Fouquay, S. Fr. Demande, 1998, FR 2755152.
17. 2S [(M+H)+]: 1723.8902; found: 1723.8935.
18. 2+]: 701.3245, found 701.3257.