Abstract
A stereospecific synthesis of N-tosyldihydroconduramine E2, a new aminocyclitol, has been synthesised starting from cyclohexa-1,3-diene. The photooxygenation of cyclohexa-1,3-diene afforded the bicyclic endoperoxide. Reduction of the endoperoxide with thiourea and then reaction of the bis-carbamate with p-TsNCO followed by a palladium-catalysed ionisation/cyclisation reaction, gave a vinyl oxazolidin-2-one. Oxidation of the double bond in the oxazolidin-2-one with KMnO4 followed by acetylation, gave the oxazolidinone-diacetates. Hydrolysis of the oxazolidinone ring and removal of the acetate groups gave the desired aminocyclitol, N-tosyldihydroconduramine E2.
References
1.
Lillelund
V.H.
,
Jenesen
H. H.
,
Liang
X. F.
, and
Bols
M.
, Chem. Rev. , 2002 , 102 , 515 .
2.
Berecibar
A.
,
Grandjean
C.
, and
Siriwardena
A.
, Chem. Rev. , 1999 , 99 , 779 .
3.
Gilbert
D.N.
, Aminoglycosides . In:
Mandell
G.L.
,
Bennet
J.E.
, and
Dolin
R.
, eds. Principles and practice of ınfectious diseases , 6th edn. Philadelphia , Churchill Livingstone , 2005 , pp. 328 .
4.
Legler
G.
, Adv. Carbohydr. Chem. Biochem. , 1990 , 48 , 319 .
5.
Jaines
B.H.
,
Elliott
N. C.
, and
Schicho
D. L.
, J. Antibiot. , 1992 , 45 , 1705 .
6.
Sakairi
N.
,
Hayashida
M.
,
Amano
A.
, and
Kuzuhara
H.
, J. Chem. Soc., Perkin Trans 1 , 1990 , 1301 .
7.
Lysek
R.
,
Schütz
C.
,
Favre
S.
,
O'Sullivan
A. C.
,
Pillonel
C.
,
Krülle
T.
,
Jung
P. M. J.
,
Clotet-Codina
I.
,
Este
J. A.
, and
Vogel
P.
, Bioorg. Med. Chem. , 2006 , 14 , 6255 .
8.
Lysek
R.
, and
Vogel
P.
, Tetrahedron , 2006 , 62 , 2733 .
9.
Miyabe
H.
,
Nishiki
A.
, and
Naito
T.
, Chem. Pharm. Bull. , 2003 , 51 , 100 .
10.
Gomez
A.M.
,
Moreno
E.
,
Valverde
S.
, and
Lopez
J. C.
, Tetrahedron Lett. , 2002 , 43 , 7863 .
11.
Sellier
O.
,
Van de Weghe
P.
,
Le Nouen
D.
,
Strehler
C.
, and
Eustache
J.
, Tetrahedron, Lett. 1999 , 40 , 853 .
12.
Mcintosh
M.C.
, and
Weinreb
S. M.
, J. Org. Chem. , 1993 , 58 , 4823 .
13.
Kresze
G.
, and
Kysela
E.
, Liebigs Ann. Chem. , 1981 , 4 , 202 .
14.
Kresze
G.
, and
Kysela
E.
, Liebigs Ann. Chem. , 1981 , 4 , 224 .
15.
Braun
H.
,
Klier
K.
,
Kresze
G.
,
Sabunu
G.
,
Werbitzky
O.
, and
Winkler
J.
, Liebigs Ann. Chem. , 1986 , 1360 .
16.
Werbitzky
O.
,
Konrad
K.
, and
Felber
H.
, Liebigs Ann. Chem. , 1990 , 267 .
17.
Hudlicky
T.
, and
Olivio
F. H.
, Tetrahedron Lett. , 1991 , 32 , 6077 .
18.
Trost
B.M.
, and
Van Vranken
D. L.
, J. Am. Chem. Soc. , 1993 , 115 , 444 .
19.
Trost
B.M.
, and
Patterson
D. E.
, Chem. Eur. J. , 1999 , 5 , 3279 .
20.
Kelebekli
L.
,
Celik
M.
,
Sahin
E.
,
Kara
Y.
, and
Balci
M.
, Tetrahedron Lett. , 2006 , 47 , 7031 .
21.
Sahin
E.
,
Kelebekli
L.
,
Kara
Y.
,
Celik
M.
, and
Balci
M.
, Acta. Crystallogr., E63. 2007 , o2464 .
22.
Kelebekli
L.
,
Kara
Y.
, and
Celik
M.
, Beilstein J. Org. Chem. , in press.
23.
Pandey
G.
,
Tiwari
S. K.
, and
Puranic
V. G.
, Org. Lett. , 2008 , 10 , 3611 .
24.
Schenck
G.O.
, and
Dunlap
D. E.
, Angew. Chem. , 1956 , 68 , 248 .
25.
Kaneko
C.
,
Sugimoto
A.
, and
Tanaka
S.
, Synthesis , 1974 , 12 , 876 .
26.
Balci
M.
, Chem. Rev. 1981 , 81 , 91 .
27.
Gültekin
M.S.
,
Celik
M.
, and
Balci
M.
, Curr. Org. Chem. , 2004 , 8 , 1159 .
28.
Kelebekli
L.
,
Kara
Y.
, and
Balci
M.
, Carbohydr. Res. , 2005 , 340 , 1940 .
29.
Trost
B.M.
,
Bernhard
B.
,
Stefan
P.
,
Jorge
Z.
, and
Joseph
W. Z.
, Angew. Chem. Int. Ed. Engl. , 1995 , 34 , 2386 .
30.
Kelebekli
L.
, J. Chem. Res. , 2008 , 104 .
31.
Kelebekli
L.
, J. Chem. Res. , 2007 , 626 .
32.
Balci
N.
,
Kelebekli
L.
,
Goksu
S.
,
Anil
B.
, and
Sahin
Ertan
, J. Chem. Res. , 2009 , 248 .
33.
Oztaskin
N.
,
Kelebekli
L.
,
Goksu
S.
,
Anil
B.
, and
Sahin
Ertan
, J. Chem. Res. , 2009 , 231 .