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Selective C-2 and C-4 deacylation and acylation of taxol: The first synthesis of a C-4 substituted taxol analogue

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
48
Identifiers
DOI: 10.1016/0040-4039(94)88392-0

Abstract

Selective hydrolysis of silylated taxol 2 with anhydrous KOH yielded 2-debenzoyl analogue 3 or 2,4-dideacyl derivative 4, depending on the reaction conditions. Reacylation provided 2-(4-chlorobenzoyl)-2-debenzoyltaxol ( 5) and 4-deacetyl-4-iso-butanoyltaxol ( 6). 1 R 1=R 4=H, R 2=COPh, R 3=Ac, taxol 2 R 1=TBS, R 2=COPh, R 3=Ac, R 4=TES 3 R 1=TBS, R 2=H, R 3=Ac, R 4=TES 4 R 1=TBS, R 2=R 3=H, R 4=TES 5 R 1=R 4=H, R 2=4-CIPhCO, R 3=Ac 6 R 1=R 4=H, R 2=COPh, R 3= iso-PrCO

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