STEREOSELECTIVE SYNTHESIS OF C-GLYCOSYL ALPHA-AMINO-ACIDS

被引:60
作者
COLOMBO, L [1 ]
CASIRAGHI, G [1 ]
PITTALIS, A [1 ]
RASSU, G [1 ]
机构
[1] CNR, IST APPLICAZ TECN CHIM AVANZATE PROBLEMI AGROBIOL, I-07100 SASSARI, ITALY
关键词
D O I
10.1021/jo00012a021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-D-C-Allosyl-(R)-alanine 12 and beta-D-C-altrosyl-(R)-alanine lactone 15 were synthesized from the common intermediate 7 in just a few steps. The beta-C-glycosyloxazolone 7 was obtained in two steps from the protected D-glucal 4 by a sequential coupling with N-benzoylalanine followed by a Claisen rearrangement.
引用
收藏
页码:3897 / 3900
页数:4
相关论文
共 15 条
[1]   (PHENYLTHIO)NITROMETHANE IN THE TOTAL SYNTHESIS OF POLYOXIN-C [J].
BARRETT, AGM ;
LEBOLD, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3853-3857
[2]   ESTER-ENOLATE CLAISEN REARRANGEMENT OF ALPHA-AMINO-ACID DERIVATIVES [J].
BARTLETT, PA ;
BARSTOW, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3933-3941
[3]   C-C LINKAGE OF CARBOXYLIC-ACIDS WITH ALLYL ALCOHOLS USING 2-PHENYLGLYCINE AS VEHICLE [J].
ENGEL, N ;
KUBEL, B ;
STEGLICH, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (06) :394-396
[4]   PYRANOSIDULOSES .8. RAPID ROUTE TO HEX-1-ENOPYRAN-3-ULOSES [J].
FRASERREID, B ;
WALKER, DL ;
TAM, SYK ;
HOLDER, NL .
CANADIAN JOURNAL OF CHEMISTRY, 1973, 51 (23) :3950-3954
[5]   GLYCOSYL ALPHA-AMINO-ACIDS VIA STEREOCONTROLLED BUILDUP OF A PENALDIC ACID EQUIVALENT - A NOVEL SYNTHETIC APPROACH TO THE NUCLEOSIDIC COMPONENT OF THE POLYOXINS AND RELATED SUBSTANCES [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3772-3787
[6]  
Hanessian S., 1983, TOTAL SYNTHESIS NATU
[7]   3-ACYLTETRAMIC ACID ANTIBIOTICS .2. SYNTHESIS OF (+)-STREPTOLIC ACID [J].
IRELAND, RE ;
SMITH, MG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) :854-860
[8]   GENERATION OF C-GLYCOSIDES THROUGH THE ENOLATE CLAISEN REARRANGEMENT [J].
IRELAND, RE ;
WILCOX, CS ;
THAISRIVONGS, S ;
VANIER, NR .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (13) :1743-1745
[9]   3-ACYLTETRAMIC ACID ANTIBIOTICS .1. SYNTHESIS OF TIRANDAMYCIC ACID [J].
IRELAND, RE ;
WUTS, PGM ;
ERNST, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3205-3207
[10]   A NEW SYNTHESIS OF ARYL MONO C-GLYCOSYL DERIVATIVES OF DIALDEHYDE SUGARS [J].
KRAUS, GA ;
SHI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4922-4925