Total synthesis of baccatin III and taxol

…, WG Bornmann, CA Alaimo, CA Coburn…

Index: 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

Full Text: HTML

Citation Number: 437

Abstract

An intramolecular Heck reaction (90→ 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland-Miescher ketone (5) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor (6). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.

Related Articles:

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 III

[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]

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

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

Enantioselective Synthesis of the Excitatory Amino Acid (1 S, 3 R)-1-Aminocyclopentane-1, 3-dicarboxylic Acid

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

More Articles...