PALLADIUM-CATALYZED REDUCTIVE DEPROTECTION OF ALLOC - TRANSPROTECTION AND PEPTIDE-BOND FORMATION

被引:50
作者
BEUGELMANS, R [1 ]
NEUVILLE, L [1 ]
BOISCHOUSSY, M [1 ]
CHASTANET, J [1 ]
ZHU, JP [1 ]
机构
[1] INST CHIM SUBST NAT,CNRS,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/0040-4039(95)00449-M
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-allyloxycarbonyl group could be efficiently removed using sodium borohyride as hydride donnor in the presence of catalytic amount of palladium (0). The conditions were applied to chemoselective protecting group transformation (transprotection) and peptide bond formation.
引用
收藏
页码:3129 / 3132
页数:4
相关论文
共 20 条
[1]   AN EASY ACCESS TO FUNCTIONALIZED DIARYL ETHERS - FORMAL TOTAL SYNTHESIS OF K-13 [J].
BEUGELMANS, R ;
BIGOT, A ;
ZHU, JP .
TETRAHEDRON LETTERS, 1994, 35 (31) :5649-5652
[2]   REDUCTIVE DEPROTECTION OF ARYL ALLYL ETHERS WITH PD(PH3)(4)/NABH4 [J].
BEUGELMANS, R ;
BOURDET, S ;
BIGOT, A ;
ZHU, JP .
TETRAHEDRON LETTERS, 1994, 35 (25) :4349-4350
[3]   SELECTIVE CLEAVAGE OF THE ALLYL AND ALLYLOXCARBONYL GROUPS THROUGH PALLADIUM-CATALYZED HYDROSTANNOLYSIS WITH TRIBUTYLTIN HYDRIDE - APPLICATION TO THE SELECTIVE PROTECTION-DEPROTECTION OF AMINO-ACID DERIVATIVES AND IN PEPTIDE-SYNTHESIS [J].
DANGLES, O ;
GUIBE, F ;
BALAVOINE, G ;
LAVIELLE, S ;
MARQUET, A .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4984-4993
[4]   TOTAL SYNTHESIS OF L-156,602, A NOVEL CYCLIC HEXADEPSIPEPTIDE ANTIBIOTIC [J].
DURETTE, PL ;
BAKER, F ;
BARKER, PL ;
BOGER, J ;
BONDY, SS ;
HAMMOND, ML ;
LANZA, TJ ;
PESSOLANO, AA ;
CALDWELL, CG .
TETRAHEDRON LETTERS, 1990, 31 (09) :1237-1240
[5]   THE OXIDATIVE MACROCYCLIZATION OF PHENOLIC PEPTIDES - A BIOMIMETIC APPROACH TO THE SYNTHESIS OF THE VANCOMYCIN FAMILY OF ANTIBIOTICS [J].
EVANS, DA ;
ELLMAN, JA ;
DEVRIES, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8912-8914
[6]  
GENET JP, 1993, SYNLETT, P680
[7]  
GREEN TW, 1991, PROTECTIVE GROUPS OR
[8]   THE ALLYLOXYCARBONYL GROUP FOR ALCOHOL PROTECTION - QUANTITATIVE REMOVAL OR TRANSFORMATION INTO ALLYL PROTECTING GROUP VIA PI-ALLYL COMPLEXES OF PALLADIUM [J].
GUIBE, F ;
SAINTMLEUX, Y .
TETRAHEDRON LETTERS, 1981, 22 (37) :3591-3594
[9]   ALLYLOXYCARBONYL GROUP - A VERSATILE BLOCKING GROUP FOR NUCLEOTIDE SYNTHESIS [J].
HAYAKAWA, Y ;
KATO, H ;
UCHIYAMA, M ;
KAJINO, H ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2400-2402
[10]   HOMOGENEOUS, PALLADIUM(0)-CATALYZED EXCHANGE DEPROTECTION OF ALLYLIC ESTERS, CARBONATES, AND CARBAMATES [J].
JEFFREY, PD ;
MCCOMBIE, SW .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :587-590