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Synthesis of [3″-3H]taxol and [13-3H]taxol1

✍ Scribed by George F. Taylor; Stephen S. Thornton; C. Ray Tallent; John A. Kepler

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
677 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

7‐Trietylsilylbaccatin III (11) was coupled with cis‐1‐benzoyl‐3‐triethylsiloxy‐4‐(3′‐bromophenyl)azetidin‐2‐one. Hydrolysis of the silyl groups gave 3″‐bromotaxol which was reduced with tritium gas to give[3″‐^3^H]taxol with specific activity of 19.3 Ci mmol. Reduction of 7‐triethylsilyl‐13‐oxobaccatin III with [^3^H]borane‐tetrahydrofuran complex gave 7‐triethylsilyl[13‐^3^H]baccatin III (17). Coupling of 17 with cis‐3‐triethylsiloxy‐4‐phenyl‐(3R,4S)‐azetidin‐2‐one and hydrolysis gave [13‐^3^H]taxol with specific activity of 1.66 Ci/mmol.

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