Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / chemistry
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Chromatography, Thin Layer
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oxidation-Reduction
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Paclitaxel / analogs & derivatives
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Paclitaxel / chemical synthesis*
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Stereoisomerism
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Taxoids*
Substances
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13-deoxybaccatin III
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Alkaloids
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Antineoplastic Agents, Phytogenic
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Taxoids
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baccatin III
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Paclitaxel