Novel biocatalytic reduction of aryl azides: Chemoenzymatic synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics

被引:51
作者
Kamal, A
Damayanthi, Y
Reddy, BSN
Lakminarayana, B
Reddy, BSP
机构
[1] Indian Inst. of Chemical Technology
关键词
D O I
10.1039/a701249g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chemoselective reduction of aryl azides to aryl amines, and the synthesis of the imine-containing pyrrolo[2,1-c]-[1,4]benzodiazepine DNA-binding antitumour antibiotics by selective biocatalytic reductive cyclization of azido aldehydes, has been achieved by employing baker's yeast.
引用
收藏
页码:1015 / 1016
页数:2
相关论文
共 22 条
[1]   A NEW CONVENIENT PROCEDURE FOR THE SYNTHESIS OF PYRROLO[2,1-C][1,4]BENZODIAZEPINES [J].
COURTNEY, SM ;
THURSTON, DE .
TETRAHEDRON LETTERS, 1993, 34 (33) :5327-5328
[2]  
CZUK R, 1991, CHEM REV, V91, P49
[3]   FACILE SYNTHESIS OF 1,4-BENZODIAZEPIN-5-ONE DERIVATIVES VIA INTRAMOLECULAR AZA-WITTIG REACTION - APPLICATION TO AN EFFICIENT SYNTHESIS OF O-BENZYL DC-81 [J].
EGUCHI, S ;
YAMASHITA, K ;
MATSUSHITA, Y ;
KAKEHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4006-4012
[4]   ON THE STERIC COURSE OF BAKER YEAST MEDIATED REDUCTION OF ALKYL 4-AZIDO-3-OXOBUTYRATE AND 4-BROMO-3-OXOBUTYRATE - SYNTHESIS OF (R)-CARNITIN AND (S)-CARNITIN [J].
FUGANTI, C ;
GRASSELLI, P ;
CASATI, P ;
CARMENO, M .
TETRAHEDRON LETTERS, 1985, 26 (01) :101-104
[5]   FACILE AND EFFICIENT SYNTHESIS OF THE DIMERS OF DC-81 ANTITUMOR ANTIBIOTICS [J].
KAMAL, A ;
RAO, NV .
TETRAHEDRON LETTERS, 1995, 36 (24) :4299-4302
[6]   SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 5-THIOABBEYMYCIN - LIMITATIONS OF THE IMINOTHIOETHER APPROACH TO CARBINOLAMINE-CONTAINING PYRROLOBENZODIAZEPINES [J].
KAMAL, A ;
REDDY, BSP ;
THURSTON, DE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (04) :743-746
[7]   ENZYMATIC DEOXIMATION OF OXIMES BY ULTRASONICALLY STIMULATED BAKER YEAST [J].
KAMAL, A ;
RAO, MV ;
MESHRAM, HM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08) :2056-2057
[8]   ENZYMATIC REGIOSPECIFIC OXIDATIVE CONVERSION OF 5-THIO TO 5-OXO BY BAKERS-YEAST IN 5,11-DITHIOPYRROLO[1,4]BENZODIAZEPINE ANTIBIOTICS [J].
KAMAL, A ;
REDDY, BSP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (03) :159-160
[9]   A new route for the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via oxidation of cyclic secondary amine [J].
Kamal, A ;
Rao, NV .
CHEMICAL COMMUNICATIONS, 1996, (03) :385-386
[10]   A new facile procedure for the preparation of pyrrolo[2,1-c] [1,4]benzodiazepines : Synthesis of the antibiotic DC-81 and its thio analogue [J].
Kamal, A ;
Reddy, BSP ;
Reddy, BSN .
TETRAHEDRON LETTERS, 1996, 37 (13) :2281-2284