Synthesis of 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III.
A one-pot trisilylation step to protect three hydroxyl groups of baccatin III (1), followed by hydride ester cleavage and base hydrolysis of a triethylsilyl ether at C13, provides efficient access to a key intermediate 9 (top path). This route removes two steps from a previously established reaction sequence to 9 (bottom path). In principle, inclusion of the truncated reaction sequence into widely utilized semisynthetic routes to next generation Taxol (paclitaxel) compounds could conceivably shorten the overall process.
Ondari
Mark E
ME
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Walker
Kevin D
KD
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D043823:Taxoids / Q000138:chemical synthesis* / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
C551686:4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III; D000470:Alkaloids; D043823:Taxoids; D014297:Trimethylsilyl Compounds; C073950:baccatin III