Synthesis and activity of a C-8 keto pleuromutilin derivative.
A C-8 keto pleuromutilin derivative has been synthesized from the biotransformation product 8-hydroxy mutilin. A key step in the process was the selective oxidation at C-8 of 8-hydroxy mutilin using tetrapropylammonium perruthenate. The presence of the C-8 keto group precipitated interesting intramolecular chemistry to afford a compound (10) with a novel pleuromutilin-derived ring system.
Springer
Dane M
DM
Department of Anti-infective Chemistry, 5 Research Parkway, PO Box 5100, Wallingford, CT 06492, USA. dspringer@rib-x.com
Sorenson
Margaret E
ME
Huang
Stella
S
Connolly
Timothy P
TP
Bronson
Joanne J
JJ
Matson
James A
JA
Hanson
Ronald L
RL
Brzozowski
David B
DB
LaPorte
Thomas L
TL
Patel
Ramesh N
RN
D001711:Biotransformation; D004224:Diterpenes / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000737:chemistry; D000097567:Pleuromutilins
D004224:Diterpenes; D007659:Ketones; D011083:Polycyclic Compounds; D000097567:Pleuromutilins; C475718:mutilin