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

…, RH Premchandran, M Rasmussen

Index: 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

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Citation Number: 19

Abstract

Functionalized erythromycin 9-oxime derivatives are 6-O-allylated under mild conditions using substituted allyl tert-butyl carbonates under palladium (0) catalysis. This allylation works well where traditional ether-forming protocols function poorly. Allyl tert-butyl carbonates provide higher yields in this reaction than lesser substituted carbonates such as ethyl or isopropyl. Aryl-substituted allyl carbonates or carbamates may be employed as ...

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The synthesis of ketolide antibiotic ABT-773 (cethromycin)

[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]

C 17, 20-Lyase inhibitors I. Structure-based de novo design ...

[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]