Baccatin III derivatives: Reduction of the C-11, C-12 double bond

A 10-Deacetylbaccatin III Derivative: 11,12-Dihydro-7-triethylsilyl-10-deacetylbaccatin III

“…2 shows the superimposition of the two molecules according to the BMFIT routine (Nyburg, 1974 Study of structure-activity relationships within the taxoid family (GuEritte-Voegelein et al, 1991) provides no information about the influence of the Cl1:=C12 double bond present in the taxane skeleton. In order to verify the importance of this bond on the conformation of the molecule and, by extension, on the biological activity with respect to its receptor, the tubulinmicrotubule system (Schiff, Fant & Horwitz, 1979), we prepared 11,12-dihydro-7-triethylsilyl-10-deacetylbaccatin HI, (3), from 10-deacetylbaccatin III in four steps (Marder, Dubois, Gu6nard, Gu6ritte-Voegelein & Potier, 1995). The dihydro derivative must be esterified at C13 with a suitable side-chain for a useful evaluation of its binding to tubulin.…”

Synthesis of Biphenyls Mimicking the Structure of the Antimitotic Rhazinilam

“…General methods were the same as previously described . All reagents were commercially available except N -( tert -butoxy-carbonyl)-2-(trimethylstannyl)aniline 10 which was prepared according to ref .…”

12,13-Isobaccatin III. Taxane Enol Esters (12,13-Isotaxanes)

“…When attempting to reduce 13-ketobaccatin III-7-O-TES ( 3 ) with zinc in acetic acid, we did not obtain the anticipated 11,12-dihydro-13-ketobaccatin III-7-O-TES ( 4 ). , Instead, following filtration and evaporation of the reaction solvent, we obtained a new compound, 5 , which was found by combustion analysis to be isomeric with 4 . The 13 C NMR spectrum of this new compound clearly lacked a signal for the C-13 carbonyl required for structure 4 and had new signals for olefinic carbons at δ 146.0 and 102.4.…”