Abstract
Trisubstituted furans have been synthesised efficiently by an alcohol substitution and dehydrogenation reaction of selenocyclic enol ethers which were prepared by organoselenium-induced regioselective electrophilic intramolecular cyclisation of allyl-substituted 1,3-dicarbonyls.
Keywords
References
1.
Dean
F.M.
, Advances in heterocyclic chemistry , ed.
Katritzky
A.R.
, Academic Press , New York , 1982 , Vol. 30 , pp. 167 –283 .
2.
Dean
F.M.
, and
Sargent
M.V.
, Comprehensive heterocyclic chemistry , eds
Bird
C.W.
, and
Cheeseman
G.W.H.
, Pergamon Press , New York , 1984 , Vol. 4 , Part 3, pp. 531 –589 .
3.
Lipshutz
B.H.
, Chem. Rev. , 1986 , 86 , 795 .
4.
Lee
J.
,
Li
J.H.
,
Oya
S.
, and
Snyder
J.K.
, J. Org. Chem. , 1992 , 57 , 5301 .
5.
Jacobi
P.A.
, and
Swlnick
H.G.
, J. Org. Chem. , 1990 , 55 , 202 .
6.
Nakanishi
K.
, Natural products chemistry , Kodansha Press , Tokyo , 1974 .
7.
Vernin
F.
, ed. The chemistry of heterocyclic favoring and aroma compounds , Ellis Horwood Press , Chichester , 1982 .
8.
Kubo
I.
,
Lee
Y.W.
,
Balogh-Nair
V.
,
Nakanishi
K.
, and
Chapya
A.
, J. Chem. Soc., Chem. Commun. , 1976 , 949 .
9.
Meyers
A.I.
, Heterocycles in organic synthesis , Wiley-Interscience Press , New York , 1974 .
10.
Lipshutz
B.H.
, Chem. Rev. , 1986 , 86 , 795 .
11.
Hou
X.L.
,
Cheung
H.Y.
,
Hon
T.Y.
,
Kwan
P.L.
,
Lo
T.H.
,
Tong
S.Y.
, and
Wong
H.N.C.
, Tetrahedron , 1998 , 54 , 1955 .
12.
Keay
B.A.
, Chem. Soc. Rev. , 1999 , 28 , 209 .
13.
Gilchrist
T.L.
, J. Chem. Soc., Perkin Trans. 1 , 1999 , 2849 .
14.
Marshall
J.A.
, and
Wang
X.J.
, J. Org. Chem. , 1992 , 57 , 3387 .
15.
Marshall
J.A.
, and
Wallace
E.M.
, J. Org. Chem. , 1995 , 60 , 796 .
16.
Mendez-Andino
J.
, and
Paquette
L.A.
, Org. Lett. , 2000 , 2 , 4095 .
17.
Brown
T.H.
,
Armitage
M.A.
,
Blakemore
R.C.
,
Blurton
P.
,
Durant
G.J.
,
Ganellin
C.R.
,
Ife
R.G.
,
Parsons
M.E.
,
Rawlings
D.A.
, and
Slingsby
B.P.
, Eur. J. Med. Chem. , 1990 , 25 , 217 .
18.
Lee
C.F.
,
Yang
L.M.
,
Hwu
T.Y.
,
Feng
A.S.
,
Tseng
J.C.
, and
Luh
T.Y.
, J. Am. Chem. Soc. , 2000 , 122 , 4992 .
19.
Kobayashi
Y.
,
Nakao
M.
,
Biju Kumar
G.
, and
Kishihara
K.
, J. Org. Chem. , 1998 , 63 , 7505 .
20.
Marshall
J.A.
, and
Robinson
E.D.
, J. Org. Chem. , 1990 , 55 , 3450 .
21.
Marshall
J.A.
, and
Bartley
G.S.
J. Org. Chem. , 1994 , 59 , 7169 .
22.
Hashmi
A.S.K.
,
Ruppert
T.L.
,
Knofel
T.
, and
Bats
J.W.
, J. Org. Chem. , 1997 , 62 , 7295 .
23.
Marshall
J.A.
, and
Sehon
C.A.
, J. Org. Chem. , 1995 , 60 , 5966 .
24.
Marshall
J.A.
, and
Sehon
C.A.
, Org. Synth. , 1998 , 76 , 263 .
25.
Gabriele
B.
,
Salerno
G.
, and
Lauria
E.
, J. Org. Chem. , 1999 , 64 , 7687 .
26.
Gabriele
B.
,
Salerno
G.
,
Pascali
F.
,
Costa
M.
, and
Chiusoli
G.P.
, J. Org. Chem. , 1999 , 64 , 7693 .
27.
Okuro
K.
,
Furuune
M.
,
Miura
M.
, and
Nomura
M.
, J. Org. Chem. , 1992 , 57 , 4754 .
28.
Sheng
H.
,
Lin
S.
, and
Huang
Y.
, Tetrahedron Lett. , 1986 , 27 , 4893 .
29.
Jeevandandam
A.
,
Narkunan
K.
,
Cartwright
C.
, and
Ling
Y.C.
, Tetrahedron Lett. , 1999 , 40 , 4841 .
30.
Matsuo
K.
, and
Sakaguchi
Y.
, Heterocycles , 1996 , 43 , 2553 .
31.
Trost
B.M.
, and
Schmidt
T.
, J. Am. Chem. Soc. , 1988 , 110 , 2301 .
32.
Ferraz
H.M.C.
,
Sano
M.K.
,
Nunes
M.R.S.
, and
Bianco
G.G.
, J. Org. Chem. , 2002 , 67 , 4122 .
33.
Tiecco
M.
,
Testaferri
L.
,
Tingoli
M.
, and
Marini
F.
, J. Org. Chem. , 1993 , 58 , 1349 .
34.
Tiecco
M.
,
Testaferri
L.
,
Tingoli
M.
, and
Bartoli
D.
, J. Org. Chem. , 1990 , 55 , 4523 .
35.
Tiecco
M.
,
Testaferri
L.
,
Tingoli
M.
, and
Marini
F.
, Synlett. , 1994 , 373 .
36.
Tiecco
M.
,
Testaferri
L.
,
Tingoli
M.
,
Chianelli
D.
, and
Bartoli
D.
, Tetrahedron , 1998 , 44 , 2273 .
37.
Tiecco
M.
,
Tingoli
M.
, and
Testaferri
L.
, Pure Appl. Chem. , 1993 , 65 , 715 .
38.
Tiecco
M.
,
Testaferri
L.
,
Marini
F.
,
Bagnoli
L.
,
Santi
C.
, and
Temperini
A.
, Tetrahedron , 1997 , 53 , 4441 .
