A STEREOSELECTIVE SYNTHESIS OF A NOVEL MODEL-COMPOUND OF CARZINOPHILIN CARRYING THE C6-C-13 UNIT WITH CORRECT STEREOCHEMISTRY

被引:26
作者
HASHIMOTO, M [1 ]
TERASHIMA, S [1 ]
机构
[1] SAGAMI CHEM RES CTR, SAGAMIHARA, KANAGAWA 229, JAPAN
关键词
D O I
10.1246/cl.1994.1001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title synthesis was achieved by featuring stereocontrolled elaboration of the functionalized pyrrolidine-2-thione from 2,3,5-tri-O-benzyl-beta-D-arabinofuranose and base-induced construction of an aziridine ring from the 5-mesyloxymethylpyrrolidine.
引用
收藏
页码:1001 / 1002
页数:2
相关论文
共 9 条
[1]   SYNTHESIS OF THE AZIRIDINO[1,2-A]PYRROLIDINE SUBSTRUCTURE OF THE ANTITUMOR AGENTS AZINOMYCIN-A AND AZINOMYCIN-B [J].
COLEMAN, RS ;
CARPENTER, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5813-5815
[2]   SYNTHESIS, CHEMICAL-REACTIVITY, AND CYTOTOXICITY OF 2-BIS(ALKOXYCARBONYL)METHYLIDEN-1-AZABICYCLO[3.1.0]HEXANE SYSTEMS RELATED TO ANTITUMOR ANTIBIOTIC CARZINOPHILIN-A [J].
HASHIMOTO, M ;
YAMADA, K ;
TERASHIMA, S .
CHEMISTRY LETTERS, 1992, (06) :975-978
[3]  
HASHIMOTO M, IN PRESS TETRAHEDRON
[4]  
HATA TOJU, 1954, JOUR ANTIBIOTICS [TOKYO], V7, P107
[5]   A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS [J].
LAY, L ;
NICOTRA, F ;
PAGANINI, A ;
PANGRAZIO, C ;
PANZA, L .
TETRAHEDRON LETTERS, 1993, 34 (28) :4555-4558
[6]   HIGHLY CONVERGENT APPROACH TO THE SYNTHESIS OF THE EPOXY-AMIDE FRAGMENT OF THE AZINOMYCINS [J].
MORAN, EJ ;
ARMSTRONG, RW .
TETRAHEDRON LETTERS, 1991, 32 (31) :3807-3810
[7]   DEHYDROAMINO ACID-DERIVATIVES FROM D-ARABINOSE AND L-SERINE - SYNTHESIS OF MODELS FOR THE AZINOMYCIN ANTITUMOR ANTIBIOTICS [J].
MORAN, EJ ;
TELLEW, JE ;
ZHAO, ZC ;
ARMSTRONG, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7848-7859
[8]  
YOKOI K, 1986, CHEM PHARM BULL, V34, P4554
[9]   OXIDATIVE REMOVAL OF N-(PARA-METHOXYBENZYL) GROUP ON DIKETOPIPERAZINE SKELETON WITH CERIC AMMONIUM-NITRATE [J].
YOSHIMURA, J ;
YAMAURA, M ;
SUZUKI, T ;
HASHIMOTO, H .
CHEMISTRY LETTERS, 1983, (07) :1001-1002