Chemistry of taxoids: One-step functionalization of the positions 1, 2, 9 and 10 from the selectively protected 5-o-cinnamoyltaxicine I

A simple one-step oxidative functionalizalion of the positions 1, 2, 9 and 10 of 5-O-cinnamoykaxicine I is described. The benzylidene and ethylidene acetals were used as protective groups on the diols 1,2 and 9,10 respectively ; their simultaneous direct conversion into 1-hydroxy-2-benzoyloxy and 9-...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 51; pp. 9189 - 9192
Main Authors Mourabit, A. Al, Poujol, H., Poupat, C., Ahond, A., Potier, P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.12.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACETALS
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Summary:A simple one-step oxidative functionalizalion of the positions 1, 2, 9 and 10 of 5-O-cinnamoykaxicine I is described. The benzylidene and ethylidene acetals were used as protective groups on the diols 1,2 and 9,10 respectively ; their simultaneous direct conversion into 1-hydroxy-2-benzoyloxy and 9-keto-10-acetoxy derivative was achieved by CrO 3/AcOH or the Jones reagent.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02152-1