Abstract
A novel synthesis route for telithromycin was developed based on a 11,12-cylic carbonate protection strategy to prevent formation of 9,12-hemiacetal by-product. Through a 11,12-carbonate-6-O-methylerythromycin intermediate, telithromycin was synthesised from 6-O-methylerythromycin in five steps with 33% overall yield.
Keywords
References
1.
Zhanel
G.G.
,
Dueck
M.
,
Hoban
D.J.
,
Vercaigne
L.M.
,
Embil
J.M.
,
Gin
A.S.
, and
Karlowsky
J.A.
, Drugs , 2001 , 61 , 443 .
2.
Leclercq
R.
, Clin. Infect. Dis. , 2002 , 34 , 482 .
3.
Pal
S.
, Tetrahedron , 2006 , 62 , 3171 .
4.
Ackermann
G.
, and
Rodloff
A.C.
, J. Antimicrob. Chemother. , 2003 , 51 , 497 .
5.
Agouridas
C.
,
Denis
A.
,
Auger
J.M.
,
Benedetti
Y.
,
Bonnefoy
A.
,
Bretin
F.
,
Chantot
J.F.
,
Dussarat
A.
,
Fromentin
C.
, and
D'Ambrières
S.G.
, J. Med. Chem. , 1998 , 41 , 4080 .
6.
Denis
A.
,
Agouridas
C.
,
Auger
J.M.
,
Benedetti
Y.
,
Bonnefoy
A.
,
Bretin
F.
,
Chantot
J.F.
,
Dussarat
A.
,
Fromentin
C.
, and
Gouin D'Ambrières
S.
, Bioorg. Med. Chem. Lett. , 1999 , 9 , 3075 .
7.
Agouridas
C.
,
Bonnefoy
A.
. USP 5527780, 1996
8.
Mordi
M.N.
,
Pelta
M.D.
,
Boote
V.
,
Morris
G.A.
, and
Barber
J.
, J. Med. Chem. , 2000 , 43 , 467 .
9.
Zhao
Y.
,
You
Q.
, and
Shen
W.
, Bioorg. Med. Chem. Lett. , 2003 , 13 , 1805 .
10.
Macher
I.
, and
De Souza
D.
. EP 2220104, 2010 .
11.
Velvadapu
V.
,
Paul
T.
,
Wagh
B.
,
Glassford
I.
,
DeBrosse
C.
, and
Andrade
R.B.
, J. Org. Chem. , 2011 , 76 , 7516 .
12.
Taber
D.F.
,
Amedio
J.C.
Jr
, and
Jung
K.Y.
, J. Org. Chem. , 1987 , 52 , 5621 .
13.
Baker
W.R.
,
Clark
J.D.
,
Stephens
R.L.
, and
Kim
K.H.
, J. Org. Chem. , 1988 , 53 , 2340 .
14.
Cao
Z.
,
Liu
B.
,
Liu
W.
,
Yao
G.
,
Li
H.
, and
Zou
T.
, J. Chem. Res. , 2011 , 35 , 600 .