Abstract
The protecting-group-free synthesis of (±)-methoxyfumimycin ethyl ester, a potential bacterial peptide deformylase (PDF) inhibitor, is reported. The synthetic approach features a tandem Friedel–Crafts alkylation/lactonisation access as a key reaction to generate α, α-disubstituted amino acid unit.
Keywords
References
1.
Kwon Y.J.
,
Sohn M.J.
,
Zheng C.J.
, and
Kim W.G.
, Org. Lett. , 2007 , 9 , 2449 .
2.
Yuan Z.
,
Trias J.
, and
White R.J.
, Drug Discovery Today. , 2001 , 6 , 954 .
3.
Waller A.S.
, and
Clements J.M.
, Curr. Opin. Drug Discovery Dev. , 2002 , 5 , 785 .
4.
Guay D.R.P.
, Ther. Clin. Risk Manage. , 2007 , 3 , 513 .
5.
Petit S.
,
Duroc Y.
,
Larue V.
,
Giglione C.
,
Leon C.
,
Soulama C.
,
Denis A.
,
Dardel F.
,
Meinnel T.
, and
Artaud I.
, ChemMedChem. , 2009 , 4 , 261 .
6.
Larue V.
,
Seijo B.
,
Tisne C.
, and
Dardel F.
, Biomol. NMR Assignments , 2009 , 3 , 153 .
7.
Gross P.J.
, and
Bräse S.
, Chem. Eur. J. , 2010 , 16 , 12660 .
8.
Gross P.J.
,
Hartmann C.E.
,
Nieger M.
, and
Bräse S.
, J. Org. Chem. , 2010 , 75 , 229 .
9.
Gross P.J.
,
Furche F.
,
Nieger M.
, and
Bräse S.
, Chem. Commun. , 2010 , 46 , 9215 .
10.
Zhou Z.W.
,
Li W.C.
,
Hu Y.
,
Wang B.
,
Ren G.
, and
Feng L.H.
, Res. Chem. Intermediat. , 2013 , 39 , 3049 .
11.
Royo E.L.P.
, and
Cativiela C.
, ARKIVOC , 2005 (VI), 46 .
12.
de la Hoz A.D.O.A.
,
Victoria Gómez M.
,
Antonio Mayoral J.
,
Moreno A.
,
Sánchez-Migallón A.M.
, and
Vázquez E.
, Tetrahedron , 2001 , 57 , 5421 .
13.
Guay D.R.P.
, Ther. Clin. Risk Manage. , 2007 , 3 , 513 .
14.
Gu K.L.
,
Bi L.R.
,
Zhao M.
,
Wang C.
,
Ju J.F.
, and
Peng S.Q.
, Bioorg. Med. Chem. , 2007 , 15 , 6273 .
