Elsevier

Tetrahedron Letters

Volume 36, Issue 11, 13 March 1995, Pages 1783-1786
Tetrahedron Letters

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

https://doi.org/10.1016/0040-4039(95)00142-YGet rights and content

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.

Reaction of paclitaxel with samarium diiodide yielded 10-deacetyl-9β-hydroxypaclitaxel (1). When docetaxel was subjected to the same reaction conditions the corresponding 9β-hydroxydocetaxel (2) and 10-dehydroxy-9β-hydroxydocetaxel (3) were isolated. Compounds 2 and 3 displayed cytotoxicities against B16 melanoma cells comparable to paclitaxel.

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