Method for preparing combretastatin

作者: Stephane Mutti , Sylviane Lutz , Marc Frederic , Joel Malpart , Philippe Masson

DOI:

关键词: Base (exponentiation)CombretastatinAmine gas treatingDerivative (chemistry)StereochemistryChemistryMedicinal chemistrySalt (chemistry)Ring (chemistry)

摘要: The invention relates to a method for preparing combretastatin (A) in the form of base or an addition salt with acid, which comprises coupling, presence and T3P, (Z)-amino compound formula (I) doubly protected L‑serine derivative (II) PG denotes group protecting amine function, so as obtain (Z)-(Ib): then deprotecting opening ring (Z)-(Ib) salt; and, optionally, adding base, having been obtained by enrichment amino (Z) isomer.

参考文章(10)
Stéphane Mutti, Michel Lavigne, Jean-Paul Casimir, Irina Malejonock, Method for preparing combretastatins ,(2003)
Koji Ohsumi, Takashi Tsuji, Kazuo Ohishi, Yoshihiro Morinaga, Stilbene derivatives and pharmaceutical compositions containing them ,(1994)
Fred Burkhart, Matthias Hoffmann, Horst Kessler, STEREOSELECTIVE SYNTHESIS OF A C-GLYCOSIDIC ANALOG OF N-GLUCOASPARAGINE Angewandte Chemie. ,vol. 36, pp. 1191- 1192 ,(1997) , 10.1002/ANIE.199711911
Kevin G Pinney, Maria P Mejia, Victor M Villalobos, Brent E Rosenquist, George R Pettit, Pascal Verdier-Pinard, Ernest Hamel, Synthesis and biological evaluation of aryl azide derivatives of combretastatin A-4 as molecular probes for tubulin. Bioorganic & Medicinal Chemistry. ,vol. 8, pp. 2417- 2425 ,(2000) , 10.1016/S0968-0896(00)00176-0
Harald Hossl, Mark Wehner, Bettina Kirschbaum, Hans Juergen Wagner, Lothar Deutscher, Method for the production of cyclic phosphonic acid anhydrides ,(2004)
Michel Lavigne, Stéphane Mutti, Irina Malejonock, Jean-Paul Casimir, Process for the preparation of combretastatins ,(2003)
George R. Pettit, Combretastatin A-4 prodrug ,(1994)
So-Yeop Han, Young-Ah Kim, Recent development of peptide coupling reagents in organic synthesis Tetrahedron. ,vol. 60, pp. 2447- 2467 ,(2004) , 10.1016/J.TET.2004.01.020