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Synthesis of [3″‐ 3 H]taxol and [13‐ 3 H]taxol 1
Author(s) -
Taylor George F.,
Thornton Stephen S.,
Tallent C. Ray,
Kepler John A.
Publication year - 1993
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580330608
Subject(s) - chemistry , hydrolysis , tetrahydrofuran , borane , silylation , medicinal chemistry , tritium , stereochemistry , organic chemistry , catalysis , physics , solvent , nuclear physics
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.