EFFICIENT METHOD FOR INTRODUCING VINEOMYCIN-FRIDAMYCIN-TYPE SIDE-CHAIN - TOTAL SYNTHESIS OF FRIDAMYCIN-E

被引:15
作者
MATSUMOTO, T [1 ]
JONA, H [1 ]
KATSUKI, M [1 ]
SUZUKI, K [1 ]
机构
[1] KEIO UNIV,DEPT CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN
关键词
D O I
10.1016/S0040-4039(00)93439-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective approach for introducing vineomycin-fridamycin-type side chain was developed. Tin-lithium exchange of arylstannane 5 followed by the reaction with chiral aldehyde 6 gave the desired adduct 7. Total synthesis of (R)-(+)-fridamycin E was accomplished.
引用
收藏
页码:5103 / 5106
页数:4
相关论文
共 16 条
[1]  
CLAUS RE, 1985, ORG SYNTH, V64, P150
[2]   GENERAL PROCEDURE FOR BASE-PROMOTED HYDROLYSIS OF HINDERED ESTERS AT AMBIENT-TEMPERATURES [J].
GASSMAN, PG ;
SCHENK, WN .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (05) :918-920
[3]  
Gschwend H.W., 1979, ORG REACT, V26, P1
[4]   ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].
HORITA, K ;
YOSHIOKA, T ;
TANAKA, T ;
OIKAWA, Y ;
YONEMITSU, O .
TETRAHEDRON, 1986, 42 (11) :3021-3028
[5]   THE STRUCTURE OF VINEOMYCIN-B-2 [J].
IMAMURA, N ;
KAKINUMA, K ;
IKEKAWA, N ;
TANAKA, H ;
OMURA, S .
JOURNAL OF ANTIBIOTICS, 1981, 34 (11) :1517-1518
[6]  
Kricke P., 1984, THESIS U GOTTINGEN THESIS U GOTTINGEN
[7]   SYNTHESIS OF RAC-FRIDAMYCIN-E AND ENT-FRIDAMYCIN-E [J].
KROHN, K ;
BALTUS, W .
TETRAHEDRON, 1988, 44 (01) :49-54
[8]  
KROHN K, 1990, TETRAHEDRON, V46, P291
[9]  
LOCHMANN L, 1966, TETRAHEDRON LETT, P257
[10]   SYNTHETIC STUDY TOWARD VINEOMYCINS - SYNTHESIS OF C-ARYL GLYCOSIDE SECTOR VIA CP2HFCL2-AGCLO4-PROMOTED TACTICS [J].
MATSUMOTO, T ;
KATSUKI, M ;
JONA, H ;
SUZUKI, K .
TETRAHEDRON LETTERS, 1989, 30 (45) :6185-6188