ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES .17. FACILE SYNTHESIS OF ETHYL ALPHA-AZIDO-ALPHA-ALKENOATES AND REDUCTION TO ETHYL ALPHA-AMINO-ALPHA-ALKENOATES

被引:23
作者
SHIN, C [1 ]
YONEZAWA, Y [1 ]
UNOKI, K [1 ]
YOSHIMURA, J [1 ]
机构
[1] TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD, MIDORI KU, YOKOHAMA 227, JAPAN
关键词
D O I
10.1246/bcsj.52.1657
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several pathways leading to ethyl α-azido-α-alkenoates (8) by the β-elimination to ethyl α-azido-β-substituted (hydroxy-, acetoxy-, or mesyloxy)-alkanoates with NaN3 or Et3N have been examined. The optimized procedure, in combination with subsequent reduction provides a general synthetic route to α-amino-α-alkenoic acid esters (9). The configuration of 8 and 9 have been shown to be of (Z)-geometry.
引用
收藏
页码:1657 / 1660
页数:4
相关论文
共 13 条
[1]  
AUWERS LV, 1923, BER, V56, P715
[2]   ORIGIN OF D-AMINO-ACIDS IN MICROBIAL PEPTIDES - RULE OF ALPHA-EPIMERIZATION [J].
BODANSZKY, M ;
PERLMAN, D .
NATURE, 1968, 218 (5138) :291-+
[3]   STRUCTURAL RELATIONSHIPS IN MICROBIAL PEPTIDES [J].
BYCROFT, BW .
NATURE, 1969, 224 (5219) :595-&
[4]   STRUCTURE OF NISIN [J].
GROSS, E ;
MORELL, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (18) :4634-+
[5]  
GROSS E, 1973, H-S Z PHYSIOL CHEM, V354, P799
[6]   BERNINAMYCIN .3. TOTAL STRUCTURE OF BERNINAMYCIN-A [J].
LIESCH, JM ;
RINEHART, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1645-1646
[7]   AMINO-ACIDS AND PEPTIDES, .20. DEHYDRO AMINO-ACIDS, .7. SYNTHESIS OF DEHYDRO AMINO-ACIDS [J].
POISEL, H .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (03) :942-947
[8]   INTENSITY FLUCTUATION SPECTROSCOPY OF DEOXYRIBONUCLEIC-ACID (DNA) .2. TEMPERATURE PROFILE OF BACTERIOPHAGE PHI29-DNA [J].
SCHMIDT, RL ;
WHITEHORN, MA ;
MAYO, JA .
BIOPOLYMERS, 1977, 16 (02) :327-340
[9]  
SCHMIDT U, 1977, ANGEW CHEM, V89, P344
[10]   ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES .13. SYNTHESIS AND CONFIGURATION OF ALKYL 2-ACYLAMINO-2-ALKENOATES AND THEIR CYCLIZED 2,5-PIPERAZINEDIONE DERIVATIVES [J].
SHIN, C ;
HAYAKAWA, M ;
SUZUKI, T ;
OHTSUKA, A ;
YOSHIMURA, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (02) :550-554