THE DIASTEREOSELECTIVE SYNTHESIS OF (+)-ACTINOBOLIN FROM D-GLUCOSE

被引:15
作者
WARD, DE
KALLER, BF
机构
关键词
ACTINOBOLIN; BACTOBOLIN; 3+3] ANNULATION; 4,6-DIDEOXY-4-GALACTOSAMINE; DIASTEREOSELECTIVE SYNTHESIS;
D O I
10.1016/0040-4039(93)85088-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The carbocyclic ring of actinobolin was constructed by a [3+3] annulation of a D-galactosamine derivative with 3-phenylthio-2-(trimethylsilylmethyl)propene. Formation of the lactone and acylation with L-alanine according to literature precedent gave (+)-actinobolin.
引用
收藏
页码:407 / 410
页数:4
相关论文
共 33 条
[21]  
NOGRADI M, 1987, STEREOSELECTIVE SYBT
[22]   SYNTHESIS OF SELECTIVELY BLOCKED ELEMENTS OF 4-AZIDO-4,6-DIDESOXY-D-GALACTOSE [J].
PAULSEN, H ;
LORENTZEN, JP .
CARBOHYDRATE RESEARCH, 1985, 140 (01) :155-162
[23]   ACTINOBOLIN VIA THE ANOMERIC EFFECT [J].
RAHMAN, MA ;
FRASERREID, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5576-5578
[24]   CHELATION OR NON-CHELATION CONTROL IN ADDITION-REACTIONS OF CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY CARBONYL-COMPOUNDS [J].
REETZ, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :556-569
[25]   SYNTHESIS AND CHEMISTRY OF 4-AMINO-4,6-DIDEOXY SUGARS .I. GALACTOSE [J].
STEVENS, CL ;
BLUMBERG.P ;
OTTERBAC.DH .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (09) :2817-&
[26]  
STRUCK RF, 1967, TETRAHEDRON LETT, P4589
[27]  
UDEA I, 1980, ACTA CRYSTALLOGR B, V36, P3128
[28]   [3+3] ANNULATION BY SEQUENTIAL 2 ELECTRON AND ONE ELECTRON ALLYLATION [J].
WARD, DE ;
KALLER, BF .
TETRAHEDRON LETTERS, 1991, 32 (07) :843-846
[29]  
WETHERINGTON JB, 1975, ACTA CRYSTALLOGR B, V31, P531
[30]   ASYMMETRIC TOTAL SYNTHESIS OF ERYTHROMYCIN .2. SYNTHESIS OF AN ERYTHRONOLIDE A LACTONE SYSTEM [J].
WOODWARD, RB ;
LOGUSCH, E ;
NAMBIAR, KP ;
SAKAN, K ;
WARD, DE ;
AUYEUNG, BW ;
BALARAM, P ;
BROWNE, LJ ;
CARD, PJ ;
CHEN, CH ;
CHENEVERT, RB ;
FLIRI, A ;
FROBEL, K ;
GAIS, HJ ;
GARRATT, DG ;
HAYAKAWA, K ;
HEGGIE, W ;
HESSON, DP ;
HOPPE, D ;
HOPPE, I ;
HYATT, JA ;
IKEDA, D ;
JACOBI, PA ;
KIM, KS ;
KOBUKE, Y ;
KOJIMA, K ;
KROWICKI, K ;
LEE, VJ ;
LEUTERT, T ;
MALCHENKO, S ;
MARTENS, J ;
MATTHEWS, RS ;
ONG, BS ;
PRESS, JB ;
RAJANBABU, TV ;
ROUSSEAU, G ;
SAUTER, HM ;
SUZUKI, M ;
TATSUTA, K ;
TOLBERT, LM ;
TRUESDALE, EA ;
UCHIDA, I ;
UEDA, Y ;
UYEHARA, T ;
VASELLA, AT ;
VLADUCHICK, WC ;
WADE, PA ;
WILLIAMS, RM ;
WONG, HNC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3213-3215