Abstract
A convenient method for the synthesis of naturally occurring 3,4-dihydroisocoumarins by judicious use of Friedel-Craft acylation, regioselective formylation and oxidative cyclisation reactions is described. O-methylated analogues of montroumarin and thunberginols C and D and have been synthesised using 3,5-dimethoxyphenylacetic acid as a starting material. Furthermore, the starting material 3,5-dimethoxyphenylacetic acid was synthesised by a route involving an oxidative Nef reaction.
References
1.
Hill
R.A.
, Progress in the chemistry of organic natural products , Vol. 48 . Springer , Verlag, Wien , 1986 .
2.
Mc Inerney
B.
, and
Taylor
W.
, Studies in natural products chemistry ,
Rahman
A.
, ed. Elsevier , New York , 1995 , Vol. 15 , 381 .
3.
Pal
S.
,
Chatare
V.
, and
Pal
M.
, Curr. Org. Chem. , 2011 , 15 , 782 .
4.
Braca
A.
,
Bader
A.
, and
Tommasi
N.
, Bioactive natural products (Part Q) Elsevier B.V. , Amsterdam , 2012 , Vol. 37 , p. 191 .
5.
Saeed
A.
,
Ashraf
Z.
, and
Rafique
H.
, J. Asian Nat. Prod. Res. , 2011 , 13 , 97 .
6.
Nozawa
K.
,
Yamada
M.
,
Tsuda
Y.
,
Kawai
K.
, and
Nakajima
S.
, Chem. Pharm. Bull. , 1981 , 29 , 2689 .
7.
Shimojima
Y.
,
Shirai
T.
,
Baba
T.
, and
Hayashi
H.
, J. Med. Chem. , 1985 , 28 , 3 .
8.
Fusetani
N.
,
Sugawara
T.
,
Matsunaga
S.
, and
Hirota
H.
, J. Org. Chem. , 1991 , 56 , 4971 .
9.
Yoshikawa
M.
,
Uchida
E.
,
Chatani
N.
,
Kobayashi
H.
,
Naitoh
Y.
,
Okuno
Y.
,
Matsuda
H.
,
Yamahara
J.
, and
Murakami
N.
, Chem. Pharm. Bull. , 1992 , 40 , 3352 .
10.
Scott
P.
, and
Van Walbeek
W.
, J. Antibiot. , 1971 , 24 , 747 .
11.
Grove
J.
, J. Chem. Soc. Perkin Trans. 1 , 1972 , 2400 .
12.
Yamato
M.
, Yakugaku. Zasshi , 1959 , 79 , 1069 .
13.
Badaruddin
A.
,
Muhammad
A.
,
Hasan
R.
,
Aslam
M.
, and
Shahid
M.
, Chin. J. Chem. , 2007 , 25 , 102 .
14.
Hisashi
M.
,
Hiroshi
S.
,
Johji
Y.
, and
Masayuki
Y.
, Bio. Pharm. Bull. , 1999 , 22 , 870 .
15.
Wang
Q.
,
Matsuda
H.
,
Matsuhira
H.
,
Nakamura
S.
,
Yuan
D.
, and
Yoshikawa
M.
, Bio. Pharm. Bull. , 2007 , 30 , 388 .
16.
Itao
C.
,
Mishina
Y.
,
Litaudon
M.
,
Cosson
J.
, and
Furukawa
H.
, Phytochemistry , 2000 , 53 , 1043 .
17.
Hamada
Y.
,
Kawai
A.
,
Kohno
Y.
,
Hara
O.
, and
Shioiri
T.
, J. Am. Chem. Soc. , 1989 , 111 , 1524 .
18.
Hamada
Y.
,
Hara
O.
,
Kawai
A.
,
Kohno
Y.
, and
Shioiri
T.
, Tetrahedron , 1991 , 47 , 8635 .
19.
Broady
S.
,
Rexhausen
J.
, and
Thomas
E.
, J. Chem. Soc. Chem. Commun. , 1991 , 708 .
20.
Broady
S.
,
Rexhausen
J.
, and
Thomas
E.
, J. Chem. Soc. Perkin Trans. 1 , 1999 , 1083 .
21.
Aamer
S.
, J. Chin. Chem. Soc. , 2003 , 50 , 313 .
22.
Uchida
K.
,
Fukuda
T.
, and
Iwao
M.
, Tetrahedron , 2007 , 63 , 7178 .
23.
Mali
R.
,
Babu
K.
, and
Jagtap
P.
, J. Chem. Soc. Perkin Trans. 1 , 2001 , 3017 .
24.
Fu
P.
,
Unruh
L.
,
Miller
D.
,
Huang
L.
, and
Yang
D.
, J. Org. Chem. , 1985 , 50 , 1259 .
25.
Mandal
S.
, and
Roy
S.
, Tetrahedron , 2008 , 64 , 11050 .
26.
Muhammad
S.
,
Ali
A.
,
Reinke
H.
, and
Langer
P.
, Tetrahedron Lett. , 2008 , 49 , 5400 .
27.
Cartor
R.
,
Coyler
R.
,
Hill
R.
, and
Staunton
J.
, J. Chem. Soc. Perkin Trans. 1. , 1976 , 1438 .
28.
Limaye
R.
,
Natu
A.
, and
Paradkar
M.
, Synth. Commun. , 2014 , 44 , 2503 .
29.
Matt
C.
,
Wagner
A.
, and
Mioskowski
C.
, J. Org. Chem. , 1997 , 234 .
30.
Kumbhar
V.
,
Joseph
A.
,
Natu
A.
,
Kusurkar
R.
, and
Paradkar
M.
, J. Chem. Res (S) , 2007 , 590 .
31.
Saeed
A.
, Z Naturforsch , 2003 , 58 , 69 .
32.
Liang
Q.
,
Zhang
J.
,
Quan
W.
,
Sun
Y.
,
She
X.
, and
Pan
X.
, J. Org. Chem. , 2007 , 72 , 2694 .
