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Synthesis of 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III
Mark E Ondari1, Kevin D Walker
1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Abstract:
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.
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