Synthesis of a novel C-10 spiro-epoxide of paclitaxel

New analogues of paclitaxel ( 1a, active constituent of Taxol®) were synthesized containing an epoxide at the C-10 position. The introduction of the epoxide was carried out by selective removal of the C10-acetate followed by protection of the C2′- and C7-hydroxyl groups. After oxidation to yield a k...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2001-07, Vol.11 (13), p.1683-1685
Hauptverfasser: Walker, Michael A., Johnson, Timothy D., Huang, Stella, Vyas, Dolatorai M., Kadow, John F.
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Sprache:eng
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Zusammenfassung:New analogues of paclitaxel ( 1a, active constituent of Taxol®) were synthesized containing an epoxide at the C-10 position. The introduction of the epoxide was carried out by selective removal of the C10-acetate followed by protection of the C2′- and C7-hydroxyl groups. After oxidation to yield a ketone at the C10-position, this intermediate was reacted with dimethylsulfonium ylide. Deprotection and further manipulations provide the C10-spiro epoxide of paclitaxel ( 1b) and the corresponding C7-MOM ether ( 1c). New analogues of paclitaxel were synthesized containing an epoxide at the C-10 position.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)00280-3