Abstract
A practical synthesis of neoponkoranol and its related sulfonium salt as potent α-glucosidase inhibitors has been developed in which the key step of coupling reaction was optimised by using isopropylidene as an effective protecting group. The characteristic intramolecular cyclisation of the coupling precursor previously encountered as a side reaction has not been detected and coupling yields were dramatically improved in the present study.
References
1.
Kordik
C.P.
, and
Reitz
A.B.
, J. Med. Chem. , 1999 , 42 , 181 .
2.
Goss
P.E.
,
Baker
M.A.
,
Carver
J.P.
, and
Dennis
J.W.
, Clin. Cancer Res. , 1995 , 1 , 935 .
3.
Broek
V.D.
, and
Leon
A.G.M.
, Carbohydrates in drug design , New York , 1997 , 471 .
4.
Cox
T.
,
Lachmann
R.
,
Hollak
C.
, and
Aerts
J.
, Lancet , 2000 , 355 , 1481 .
5.
Yoshikawa
M.
,
Murakami
T.
,
Shimada
H.
,
Tanabe
G.
, and
Muraoka
O.
, Tetrahedron Lett. , 1997 , 38 , 8367 .
6.
Yoshikawa
M.
,
Morikawa
T.
,
Matsuda
H.
,
Tanabe
G.
, and
Muraoka
O.
, Bioorg. Med. Chem. , 2002 , 10 , 1547 .
7.
Yoshikawa
M.
,
Xu
F.
,
Nakamura
S.
,
Wang
T.
,
Matsuda
H.
,
Tanabe
G.
, and
Muraoka
O.
, Heterocycles , 2008 , 75 , 1397 .
8.
Yoshikawa
M.
,
Murakami
T.
,
Yashiro
K.
, and
Matsuda
H.
, Chem. Pharm. Bull. , 1998 , 46 , 1339 .
9.
Ozaki
S.
,
Oe
H.
, and
Kitamura
S.
, J. Nat. Prod. , 2008 , 71 , 981 .
10.
Xie
W.
,
Tanabe
G.
,
Akaki
J.
,
Morikawa
T.
,
Ninomiya
K.
,
Minematsu
T.
,
Yoshikawa
M.
,
Wu
X.
, and
Muraoka
O.
, Bioorg. Med. Chem. , 2011 , 19 , 2015 .
11.
Minami
Y.
,
Kuriyama
C.
,
Ikeda
K.
,
Kato
A.
,
Takebayashi
K.
,
Adachi
I.
,
Fleet
W.J.G.
,
Kettawan
A.
,
Okamoto
T.
, and
Asano
N.
, Bioorg. Med. Chem. , 2008 , 16 , 2734 .
12.
Sim
L.
,
Jayakanthan
K.
,
Mohan
S.
,
Nasi
R.
,
Johnston
B.D.
,
Pinto
B.M.
, and
Rose
D.R.
, Biochemistry , 2010 , 49 , 443 .
13.
Nakamura
S.
,
Takahira
K.
,
Tanabe
G.
,
Morikawa
T.
,
Sakano
M.
,
Ninomiya
K.
,
Yoshikawa
M.
,
Muraoka
O.
, and
Nakanishi
I.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 4420 .
14.
Tanabe
G.
,
Otani
T.
,
Cong
W.
,
Minematsu
T.
,
Ninomiya
K.
,
Yoshikawa
M.
,
Muraoka
O.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 3159 .
15.
Tanabe
G.
,
Nakamura
S.
,
Tsutsui
N.
,
Balakishan
G.
,
Xie
W.
,
Tsuchiya
S.
,
Akaki
J.
,
Morikawa
T.
,
Ninomiya
K.
,
Nakanishi
I.
,
Yoshikawa
M.
, and
Muraoka
O.
, Chem. Commun. , 2012 , 48 , 8646 .
16.
Tanabe
G.
,
Matsuoka
K.
,
Yoshinaga
M.
,
Xie
W.
,
Tsutsui
N.
,
Amer
M.F.A.
,
Nakamura
S.
,
Nakanishi
I.
,
Wu
X.
,
Yoshikawa
M.
, and
Muraoka
O.
, Bioorg. Med. Chem. , 2012 , 20 , 6321 .
17.
Xie
W.
,
Tanabe
G.
,
Kinjyo
E.
,
Minematsu
T.
,
Wu
X.
,
Yoshikawa
M.
,
Muraoka
O.
, Bioorg. Med. Chem. , 2011 , 19 , 2252 .
18.
Xie
W.
,
Tanabe
G.
,
Xu
J.
,
Wu
X.
,
Morikawa
T.
,
Yoshikawa
M.
, and
Muraoka
O.
, Mini-Rev. Org. Chem. , 2013 , 10 , 141 .
19.
Cimetiere
B.
,
Jacob
L.
, and
Julia
M.
, Tetrahedron Lett. , 1986 , 27 , 6329 .
20.
Cimetiere
B.
,
Jacob
L.
, and
Julia
M.
, Bull. Soc. Chim. Fr. , 1991 , 128 , 926 .
21.
Okuma
K.
,
Nakamura
S.
, and
Ohta
H.
, Heterocycles , 1987 , 26 , 2343 .
22.
Eskandari
R.
,
Kuntz
D.A.
,
Rose
D.R.
, and
Pinto
B.M.
, Org. Lett. , 2010 , 12 , 1632 .
23.
Nieves
R.P.
,
Andres
G.S.
,
Cosme
G.F.
,
Ernesto
S.
, and
Concepcion
C.G.
, Org. Lett. , 2012 , 14 , 3388 .
24.
Giuditta
B.
,
Roberto
B.
,
Giorgio
C.
,
Felicia
D.A.
, and
Lorenzo
G.
, Eur. J. Org. Chem. , 2007 , 588 .