Synthesis of pyrrolobenzodiazepines via the PIFA oxidation of amines. Synthesis of 8-deoxy DC-81

被引:21
作者
Kraus, GA [1 ]
Melekhov, A [1 ]
机构
[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1016/S0040-4020(98)83036-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PIFA can be used to introduce the imine moiety into a precursor to the pyrrolobenzodiazepines in 62% yield. This oxidation completes an efficient four-step synthesis of 8-deoxy DC-81. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:11749 / 11754
页数:6
相关论文
共 10 条
[1]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[2]   Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics: Oxidation of cyclic secondary amine with TPAP [J].
Kamal, A ;
Howard, PW ;
Reddy, BSN ;
Reddy, BSP ;
Thurston, DE .
TETRAHEDRON, 1997, 53 (09) :3223-3230
[3]   A DIRECT ROUTE TO THE PYRROLO[2,1-C][1,4]BENZODIAZEPINE RING-SYSTEM USING ARYL TRIFLATES [J].
KRAUS, GA ;
LIU, P .
TETRAHEDRON LETTERS, 1995, 36 (42) :7595-7598
[4]  
LIU P, 1995, THESIS IOWA STATE U
[5]   HYPERVALENT IODINE OXIDATION OF PARA-ALKOXYPHENOLS AND RELATED-COMPOUNDS - A GENERAL-ROUTE TO PARA-BENZOQUINONE MONOACETALS AND SPIRO LACTONES [J].
TAMURA, Y ;
YAKURA, T ;
HARUTA, J ;
KITA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3927-3930
[6]  
Thurston D.E., 1993, MOL ASPECTS ANTICANC, P54
[7]  
Thurston D. E. H., 1983, DRUGS FUTURE, V8, P957
[8]   SYNTHESIS AND STEREOCHEMISTRY OF CARBINOLAMINE-CONTAINING PYRROLO[1,4]BENZODIAZEPINES BY REDUCTIVE CYCLIZATION OF N-(2-NITROBENZOYL)PYRROLIDINE-2-CARBOXALDEHYDES [J].
THURSTON, DE ;
LANGLEY, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :705-712
[9]   SYNTHESIS OF DNA-INTERACTIVE PYRROLO[2,1-C][1,4]BENZODIAZEPINES [J].
THURSTON, DE ;
BOSE, DS .
CHEMICAL REVIEWS, 1994, 94 (02) :433-465
[10]   SYNTHETIC STUDIES OF THE PYRROLOQUINOLINE NUCLEUS OF THE MAKALUVAMINE ALKALOIDS - SYNTHESIS OF THE TOPOISOMERASE-II INHIBITOR MAKALUVAMINE-D [J].
WHITE, JD ;
YAGER, KM ;
YAKURA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1831-1838