SB-RA-31012011

Chemical Name: 3-Methoxybenzoic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,9,12b-tris(acetoxy)-4-[3-(4-benzoylphenyl)-2(E)-propenoyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-1
项目整合开发状态: Biological Testing
项目研究机构: Roswell Park Memorial Inst. (Originator), State University of New York,Stony Brook (Originator)
合成路线:10-Deacetylbaccatin III (I) was protected by treatment with triethylsilyl chloride and imidazole,and the resulting trisilylated compound (II) was debenzoylated to diol (III) by using Red-Al(R).Coupling of (III) with m-anisic acid (IV) yielded the m-methoxybenzoate ester (V).Complete desilylation of (V),followed by selective resilylation at C-7 with triethylsilyl chloride,furnished (VI).Acylation at C-10 and C-13 by means of Ac2O and DMAP,followed by desilylation,gave the modified baccatin (VII).

合成路线:Heck coupling between 4-bromobenzophenone (VIII) and methyl acrylate (IX) in the presence of palladium diacetate gave the unsaturated ester (X).Subsequent basic hydrolysis of the methyl ester group of (X) yielded p-benzoylcinnamic acid (XI).The title compound was then obtained by the coupling of acid (XI) with the precursor baccatin (VII) in the presence of EDC and DMAP.