STEREOSELECTIVE SYNTHESIS OF (2S,3S,4R)-4-AMINO-3-HYDROXY-2-METHYL-PENTANOIC ACID, AN AMINO-ACID CONSTITUENT OF BLEOMYCIN, BY ALDOL CONDENSATION

被引:38
作者
NARITA, M
OTSUKA, M
KOBAYASHI, S
OHNO, M
UMEZAWA, Y
MORISHIMA, H
SAITO, SI
TAKITA, T
UMEZAWA, H
机构
[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN
[2] INST MICROBIAL CHEM,SHINAGAWA KU,TOKYO 141,JAPAN
关键词
D O I
10.1016/S0040-4039(00)86879-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:525 / 528
页数:4
相关论文
共 18 条
[1]   STUDIES IN STEROECHEMISTRY .32. MODELS FOR 1,2-ASYMMETRIC INDUCTION [J].
CRAM, DJ ;
WILSON, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (09) :1245-&
[2]   ACYCLIC STEREOSELECTION .4. ASSIGNMENT OF STEREOSTRUCTURE TO BETA-HYDROXYCARBONYL COMPOUNDS BY C-13 NUCLEAR MAGNETIC-RESONANCE [J].
HEATHCOCK, CH ;
PIRRUNG, MC ;
SOHN, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4294-4299
[3]  
HIRAMA M, 1979, TETRAHEDRON LETT, P3937
[4]   PEPTIDES .6. SOME OXIME CARBONATES AS NOVEL TERT-BUTOXYCARBONYLATING REAGENTS [J].
ITOH, M ;
HAGIWARA, D ;
KAMIYA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (03) :718-721
[5]   STEREOSELECTIVE ALDOL CONDENSATION - USE OF CHIRAL BORON ENOLATES [J].
MASAMUNE, S ;
CHOY, W ;
KERDESKY, FAJ ;
IMPERIALI, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) :1566-1568
[6]   CHEMISTRY OF BLEOMYCIN .6. SELECTIVE CLEAVAGE OF BLEOMYCIN A2 BY N-BROMOSUCCINIMIDE [J].
MURAOKA, Y ;
UMEZAWA, H ;
TAKITA, T ;
MAEDA, K .
JOURNAL OF ANTIBIOTICS, 1972, 25 (03) :185-&
[7]   NEW AGENTS FOR TERTIARY BUTYLOXYCARBONYLATION AND PARA METHOXYBENZYL-OXYCARBONYLATION OF AMINO-ACIDS [J].
NAGASAWA, T ;
KUROIWA, K ;
NARITA, K ;
ISOWA, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (04) :1269-1272
[8]   A SIMPLE PREPARATION OF PHTHALOYL AMINO ACIDS VIA A MILD PHTHALOYLATION [J].
NEFKENS, GHL ;
TESSER, GI ;
NIVARD, RJF .
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1960, 79 (06) :688-698
[9]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF BESTATIN ANALOGS, INHIBITORS OF AMINOPEPTIDASE-B [J].
NISHIZAWA, R ;
SAINO, T ;
TAKITA, T ;
SUDA, H ;
AOYAGI, T ;
UMEZAWA, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (04) :510-515
[10]   (2S,3S,4R)-4-AMINO-3-HYDROXY-2-METHYLVALERATE - SYNTHESIS OF AN AMINO-ACID CONSTITUENT OF BLEOMYCIN FROM L-RHAMNOSE [J].
OHGI, T ;
HECHT, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1232-1234