Synthetic studies with 13-deoxybaccatin III.
An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI(2), produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D017239:Paclitaxel / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism; D043823:Taxoids
C472227:13-deoxybaccatin III; D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D043823:Taxoids; C073950:baccatin III; D017239:Paclitaxel