Synthesis of carbon??14 labeled Taxol®(paclitaxel)

…, JE Swigor, J Kant, DR Schroeder

Index: Walker; Swigor; Kant; Schroeder Journal of Labelled Compounds and Radiopharmaceuticals, 1994 , vol. 34, # 10 p. 973 - 980

Full Text: HTML

Citation Number: 1

Abstract

Abstract Reductive cleavage of the C13 side chain of Taxol®(1, paclitaxel) followed by regioselective silylation gave 7-triethylsilylbaccatin III (4). 3-O-Triethylsilylation of 5 and subsequent reaction with benzoyl chloride-C7-14 C gave azetidinone 7. Coupling of 4 and 7 followed by deprotection gave 1.26 g of Taxol®-N3′-14 C (11) having a specific activity of 26.5 mCi/mmol and a radiochemical purity of 95%.

~80%

~97%

Total synthesis of baccatin III and taxol

[Danishefsky, Samuel J.; Masters, John J.; Young, Wendy B.; Link; Snyder, Lawrence B.; Magee, Thomas V.; Jung, David K.; Isaacs, Richard C. A.; Bornmann, William G.; Alaimo, Cheryl A.; Coburn, Craig A.; Di Grandi, Martin J. Journal of the American Chemical Society, 1996 , vol. 118, # 12 p. 2843 - 2859]

Asymmetric Total Synthesis of Taxol\ R

[Shiina, Isamu; Iwadare, Hayato; Sakoh, Hiroki; Hasegawa, Masatoshi; Tani, Yu-Ichirou; Mukaiyama, Teruaki Chemistry Letters, 1998 , # 1 p. 1 - 2]

Modified taxols. 3. Preparation and acylation of baccatin II...

[Magri, Neal F.; Kingston, David G.I.; Jitrangsri, Chote; Piccariello, Thomas Journal of Organic Chemistry, 1986 , vol. 51, # 16 p. 3239 - 3242]

Asymmetric Total Synthesis of Taxol\ R

[Shiina, Isamu; Iwadare, Hayato; Sakoh, Hiroki; Hasegawa, Masatoshi; Tani, Yu-Ichirou; Mukaiyama, Teruaki Chemistry Letters, 1998 , # 1 p. 1 - 2]

Enantioselective Synthesis of the Excitatory Amino Acid (1 S...

[Shiina, Isamu; Saitoh, Masahiro; Nishimura, Koji; Saitoh, Katsuyuki; Mukaiyama, Teruaki Chemistry Letters, 1996 , # 3 p. 223 - 224]