Allylation of erythromycin derivatives: introduction of allyl substituents into highly hindered alcohols.
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 well and, when used, produce trans-olefinic products.
Stoner
Eric J
EJ
Global Pharmaceutical Research and Development, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-6290, USA. eric.stoner@abbott.com
Peterson
Matthew J
MJ
Allen
Michael S
MS
DeMattei
John A
JA
Haight
Anthony R
AR
Leanna
M Robert
MR
Patel
Subhash R
SR
Plata
Daniel J
DJ
Premchandran
Ramiya H
RH
Rasmussen
Michael
M
D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D004917:Erythromycin / Q000737:chemistry*
D000438:Alcohols; D004917:Erythromycin