Mild nitrosation and hydrolysis of polyfunctional amides

被引:66
作者
Evans, DA
Carter, PH
Dinsmore, CJ
Barrow, JC
Katz, JL
Kung, DW
机构
[1] Dept. of Chem. and Chemical Biology, Harvard University, Cambridge
关键词
D O I
10.1016/S0040-4039(97)00972-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Secondary amides may be hydrolyzed via a mild, high-yielding sequence consisting of N-nitrosation, treatment with lithium hydroperoxide, and reduction with sodium sulfite. These operations may be executed in the presence of an array of functional groups, including other amide functionality. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4535 / 4538
页数:4
相关论文
共 32 条
[1]  
BERENGUER R, 1989, SYNTHESIS-STUTTGART, P305
[2]   Synthesis of the orienticin C M(2-4) macrocycle utilizing a nucleophilic aromatic substitution strategy [J].
Evans, DA ;
Watson, PS .
TETRAHEDRON LETTERS, 1996, 37 (19) :3251-3254
[3]   SYNTHESIS OF 1,3-DIOL SYNTHONS FROM EPOXY AROMATIC PRECURSORS - AN APPROACH TO THE CONSTRUCTION OF POLYACETATE-DERIVED NATURAL-PRODUCTS [J].
EVANS, DA ;
GAUCHETPRUNET, JA ;
CARREIRA, EM ;
CHARETTE, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :741-750
[4]   CONTROL OF REMOTE ENOATE GEOMETRY IN THE BRYOSTATINS WITH A TETHERED HORNER-WADSWORTH-EMMONS REAGENT [J].
EVANS, DA ;
CARREIRA, EM .
TETRAHEDRON LETTERS, 1990, 31 (33) :4703-4706
[5]   OXIDATIVE COUPLING OF ARYLGLYCINE-CONTAINING PEPTIDES - A BIOMIMETIC APPROACH TO THE SYNTHESIS OF THE MACROCYCLIC ACTINOIDINIC-CONTAINING VANCOMYCIN SUBUNIT [J].
EVANS, DA ;
DINSMORE, CJ ;
EVRARD, DA ;
DEVRIES, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6426-6427
[6]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[7]  
EVANS DA, 1997, IN PRESS J AM CHEM S, V119
[8]   A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS [J].
FLYNN, DL ;
ZELLE, RE ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2424-2426
[9]   Concise synthesis of taxol A-ring components: Remote diastereoselective additions of alkenyl lithiums to aldehydes [J].
Frost, C ;
Linnane, P ;
Magnus, P ;
Spyvee, M .
TETRAHEDRON LETTERS, 1996, 37 (51) :9139-9142
[10]   NITROSATION OF PEPTIDE-BONDS - CLEAVAGE OF NITROSATED PEPTIDES BY PYRROLIDINE AND ALPHA-AMINO ESTERS [J].
GARCIA, J ;
GONZALEZ, J ;
SEGURA, R ;
VILARRASA, J .
TETRAHEDRON, 1984, 40 (16) :3121-3127