Abstract
The first total synthesis of the furanolactam fuscain is reported. The key step in the synthesis was the formation of seven-membered lactam by acylation of a furan ring using the mild Lewis acid CuSO4·5H2O.
References
1.
Zeng L.M.
,
Zhu Y.
,
Yan S.J.
, and
Su J.Y.
, Chem. Res. Chinese Univ. , 1998 , 14 , 426 .
2.
Zeng L.M.
,
Fu X.
,
Su J.Y.
,
Guzman F.D.
,
Schmitz J.F.
,
Hossain M.B.
,
Helm D.V.D.
, Chin. J. Chem. , 1991 , 9 , 136 .
3.
Zhang B.B.
, and
Moller D.E.
, Curr. Opin. Chem. Biol. , 2000 , 4 , 461 .
4.
Phuwapraisirsan P.
,
Matsunaga S.
,
van Soest R.W.M.
, and
Fusetani N.
, Tetrahedron Lett. , 2004 , 45 , 2125 .
5.
Wang X.
,
Bastow K.F.
,
Sun C.M.
,
Lin Y.L.
,
Yu H.J.
,
Don M.J.
,
Wu T.S.
,
Nakamura S.
, and
Lee K.H.
, J. Med. Chem. , 2004 , 47 , 5816 .
6.
Kernan M.R.
, and
Faulkner D.J.
, J. Org. Chem. , 1988 , 53 , 4574 .
7.
Kimura J.
,
Ishizuka E.
,
Nakao Y.
,
Yoshida W.Y.
,
Scheuer P.J.
, and
Kelly-Borges M.
, J. Nat. Prod. , 1998 , 61 , 248 .
8.
Nakamura M.
,
Kakuda T.
,
Oba Y.
,
Ojika M.
, and
Nakamura H.
, Bioorg. Med. Chem. , 2003 , 11 , 3077 .
9.
Laurent D.
,
Jullian V.
,
Parenty A.
,
Knibiehler M.
,
Dorin D.
,
Schmitt S.
, and
Lozach O.
, Bioorg. Med. Chem. , 2006 , 14 , 4477 .
10.
Kimura J.
,
Ishizuka E.
,
Nakao Y.
,
Yoshida W.Y.
,
Scheuer P.J.
, and
Kelly-Borges M.
, J. Nat. Prod. , 1998 , 61 , 248 .
11.
Kohmoto S.
,
McConnell O.J.
,
Wright A.
, and
Cross S.
, Chem. Lett. , 1987 , 9 , 1687 .
12.
Xie J.W.
,
Tian J.Y.
,
Su L.
,
Huang M.N.
,
Zhu X.H.
,
Ye F.
, and
Wan Y.Q.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 4306 .
13.
Calloway N.O.
, Chem. Rev. , 1935 , 17 , 327 .
14.
Wilkinson M.C.
, Org. Lett. , 2011 , 13 , 2232 .
15.
Ouyang W.Z.
,
Guo Z.C.
,
Du Y.G.
, and
Tan C.Y.
, Chem. Res. Appl. , 2008 , 20 , 290 .
16.
Li H.C.
,
Wang C.
,
Sanchez T.
,
Tan Y.M.
, and
Jiang C.Y.
, Bioorg. Med. Chem. , 2009 , 17 , 2913 .
17.
Calderone V.
,
Fiamingo F.L.
,
Giorgi I.
,
Leonardi M.
,
Livi O.
, and
Martelli A.
, Eur. J. Med. Chem. , 2006 , 41 , 761 .