Stereoselective synthesis of 9β-hydroxytaxanes via reduction with samarium diiodide

Gunda I. Georg; Zacharia S. Cheruvallath; David G. Vander Velde; Richard H. Himes

doi:10.1016/0040-4039(95)00142-Y

Stereoselective synthesis of 9β-hydroxytaxanes via reduction with samarium diiodide

Gunda I. Georg, Zacharia S. Cheruvallath, David G. Vander Velde, Richard H. Himes

Medicinal Chemistry

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Abstract

Reaction of baccatin III and paclitaxel with samarium diiodide yielded the corresponding 10-deacetyl-9β-hydroxy derivatives. When 10-deacetylbaccatin III and docetaxel were subjected to the same reaction conditions the corresponding 9β-hydroxy and 10-dehydroxy-9β-hydroxy analogues were isolated.

Original language	English (US)
Pages (from-to)	1783-1786
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	11
DOIs	https://doi.org/10.1016/0040-4039(95)00142-Y
State	Published - Mar 13 1995

Bibliographical note

Funding Information:
Acknowledgements: We gratefully acknowledge financial support from the National Institutes of Health (CA55160 and CA55141). Support is also acknowledged from the Kansas Health Foundation for a postdoctoral fellowship awarded to Z. S. Cheruvallath. Dr. S. M. Ali is acknowledged for providing a sample of docetaxel for these studies, Dr. M. Morton and Dr. S. M. Ali for their help with the NMR studies, and Drs. G. C. B. Harriman and T. C. Boge for helpful discussions. Paclitaxel and a mixture of paelitaxel and cephalomannine were provided to us for these studies by the National Cancer Institute.

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title = "Stereoselective synthesis of 9β-hydroxytaxanes via reduction with samarium diiodide",

abstract = "Reaction of baccatin III and paclitaxel with samarium diiodide yielded the corresponding 10-deacetyl-9β-hydroxy derivatives. When 10-deacetylbaccatin III and docetaxel were subjected to the same reaction conditions the corresponding 9β-hydroxy and 10-dehydroxy-9β-hydroxy analogues were isolated.",

author = "Georg, {Gunda I.} and Cheruvallath, {Zacharia S.} and {Vander Velde}, {David G.} and Himes, {Richard H.}",

note = "Funding Information: Acknowledgements: We gratefully acknowledge financial support from the National Institutes of Health (CA55160 and CA55141). Support is also acknowledged from the Kansas Health Foundation for a postdoctoral fellowship awarded to Z. S. Cheruvallath. Dr. S. M. Ali is acknowledged for providing a sample of docetaxel for these studies, Dr. M. Morton and Dr. S. M. Ali for their help with the NMR studies, and Drs. G. C. B. Harriman and T. C. Boge for helpful discussions. Paclitaxel and a mixture of paelitaxel and cephalomannine were provided to us for these studies by the National Cancer Institute.",

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AU - Georg, Gunda I.

AU - Cheruvallath, Zacharia S.

AU - Vander Velde, David G.

AU - Himes, Richard H.

N1 - Funding Information: Acknowledgements: We gratefully acknowledge financial support from the National Institutes of Health (CA55160 and CA55141). Support is also acknowledged from the Kansas Health Foundation for a postdoctoral fellowship awarded to Z. S. Cheruvallath. Dr. S. M. Ali is acknowledged for providing a sample of docetaxel for these studies, Dr. M. Morton and Dr. S. M. Ali for their help with the NMR studies, and Drs. G. C. B. Harriman and T. C. Boge for helpful discussions. Paclitaxel and a mixture of paelitaxel and cephalomannine were provided to us for these studies by the National Cancer Institute.

PY - 1995/3/13

Y1 - 1995/3/13

N2 - Reaction of baccatin III and paclitaxel with samarium diiodide yielded the corresponding 10-deacetyl-9β-hydroxy derivatives. When 10-deacetylbaccatin III and docetaxel were subjected to the same reaction conditions the corresponding 9β-hydroxy and 10-dehydroxy-9β-hydroxy analogues were isolated.

AB - Reaction of baccatin III and paclitaxel with samarium diiodide yielded the corresponding 10-deacetyl-9β-hydroxy derivatives. When 10-deacetylbaccatin III and docetaxel were subjected to the same reaction conditions the corresponding 9β-hydroxy and 10-dehydroxy-9β-hydroxy analogues were isolated.

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JO - Tetrahedron Letters

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IS - 11

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Stereoselective synthesis of 9β-hydroxytaxanes via reduction with samarium diiodide

Abstract

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