Stereospecific synthesis of 7-deoxy-6-hydroxy paclitaxel

The synthetic transposition of the 7-hydroxyl group of paclitaxel to the 6-position is described. The route presented prepares both the 6-α- and β-isomers stereospecifically. The key step of this transposition involves the stereoselective reduction of the 6,7-α-thiocarbonate using tributylgermanium...

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Bibliographic Details
Published in:Tetrahedron letters 1999-07, Vol.40 (27), p.4943-4946
Main Authors: Wittman, Mark D., Alstadt, Thomas J., Kadow, John F., Vyas, Dolatrai M., Johnson, Kathy, Fairchild, Craig, Long, Byron
Format: Article
Language:English
Subjects:
deoxygenation
germanium compounds
taxoids
thiocarbonates
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Summary:The synthetic transposition of the 7-hydroxyl group of paclitaxel to the 6-position is described. The route presented prepares both the 6-α- and β-isomers stereospecifically. The key step of this transposition involves the stereoselective reduction of the 6,7-α-thiocarbonate using tributylgermanium hydride. The synthetic transposition of the 7-hydroxyl of paclitaxel to the 6 position is accomplished via a regioselective deoxgenation of a cyclic thiocarbonate. Both 6-hydroxyl isomers are stereospecifically synthesized.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00864-3