Tetrahedron

The synthesis of ketolide antibiotic ABT-773 (cethromycin)

DJ Plata, MR Leanna, M Rasmussen, MA McLaughlin…

Index: Plata, Daniel J.; Leanna, M. Robert; Rasmussen, Michael; McLaughlin, Maureen A.; Condon, Steven L.; Kerdesky, Francis A.J.; King, Steven A.; Peterson, Matthew J.; Stoner, Eric J.; Wittenberger, Steven J. Tetrahedron, 2004 , vol. 60, # 45 p. 10171 - 10180

Full Text: HTML

Citation Number: 31

Abstract

A practical and efficient synthesis of ketolide antibiotic cethromycin (ABT-773)() is described. An effective protection strategy allows high yielding, regioselective C6-O-alkylation and subsequent stereoselective modification of the erythromycin nucleus. ABT-773 was prepared in 10 steps from commercially available erythromycin A oxime.

Related Articles:

Allylation of erythromycin derivatives: introduction of allyl substituents into highly hindered alcohols

[Stoner, Eric J.; Peterson, Matthew J.; Allen, Michael S.; DeMattei, John A.; Haight, Anthony R.; Leanna, M. Robert; Patel, Subhash R.; Plata, Daniel J.; Premchandran, Ramiya H.; Rasmussen, Michael Journal of Organic Chemistry, 2003 , vol. 68, # 23 p. 8847 - 8852]

C 17, 20-Lyase inhibitors I. Structure-based de novo design and SAR study of C 17, 20-lyase inhibitors

[Matsunaga, Nobuyuki; Kaku, Tomohiro; Itoh, Fumio; Tanaka, Toshimasa; Hara, Takahito; Miki, Hiroshi; Iwasaki, Masahiko; Aono, Tetsuya; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro Bioorganic and medicinal chemistry, 2004 , vol. 12, # 9 p. 2251 - 2273]

More Articles...