Synthesis of the diazepanone-nucleoside portion of liposidomycins by aldol reaction of the enolate of diazepanone with a nucleoside 5′-aldehyde

被引：30

作者：

Kim, KS ^{[1
]}

Ahn, YH ^{[1
]}

机构：

[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 20期

关键词：

D O I：

10.1016/S0957-4166(98)00366-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diazepanone-nucleoside part of liposidomycins has been synthesized by the aldol reaction between the enolate of a stereochemically defined diazepanone and a uridine 5'-aldehyde. The configurations of two new stereocenters in the aldol product have been assigned on the basis of the H-1 NMR coupling constants and NOE of its derivative. (C) 1998 Elsevier Science Ltd. AII rights reserved.

引用

收藏

页码：3601 / 3605

页数：5

相关论文

共 15 条

[1] AN ENZYME-SUBSTRATE COMPLEX INVOLVED IN BACTERIAL-CELL WALL BIOSYNTHESIS [J].

BENSON, TE ;

FILMAN, DJ ;

WALSH, CT ;

HOGLE, JM .

NATURE STRUCTURAL BIOLOGY, 1995, 2 (08) :644-653

[2] FULLY SYNTHETIC STEREOSELECTIVE ROUTES TO THE DIFFERENTIALLY PROTECTED SUBUNITS OF THE TUNICAMYCINS [J].

DANISHEFSKY, SJ ;

DENINNO, SL ;

CHEN, S ;

BOISVERT, L ;

BARBACHYN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5810-5818

[3] ACYCLIC STEREOSELECTION .7. STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXY CARBONYL-COMPOUNDS BY ALDOL CONDENSATION [J].

HEATHCOCK, CH ;

BUSE, CT ;

KLESCHICK, WA ;

PIRRUNG, MC ;

SOHN, JE ;

LAMPE, J .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1066-1081

[4] LIPOSIDOMYCINS - NOVEL NUCLEOSIDE ANTIBIOTICS WHICH INHIBIT BACTERIAL PEPTIDOGLYCAN SYNTHESIS [J].

ISONO, K ;

URAMOTO, M ;

KUSAKABE, H ;

KIMURA, KI ;

IZAKI, K ;

NELSON, CC ;

MCCLOSKEY, JA .

JOURNAL OF ANTIBIOTICS, 1985, 38 (11) :1617-1621

[5]

Kim KS, 1997, B KOR CHEM SOC, V18, P465

[6]

KIM KS, 1994, B KOR CHEM SOC, V15, P829

[7] SYNTHESIS OF THE 1,4-DIAZEPAN-2-ONE MOIETY OF LIPOSIDOMYCINS [J].

KIM, KS ;

CHO, IH ;

AHN, YH ;

ILPARK, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (14) :1783-1785

[8] SYNTHETIC STUDIES OF THE 5-AMINOPENTOSE 2-SULFATE COMPONENT OF THE LIPOSIDOMYCINS [J].

KIM, KS ;

LIM, JW ;

JOO, YH ;

KIM, KT ;

CHO, IH ;

AHN, YH .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (03) :439-443

[9] LIPOSIDOMYCIN-C INHIBITS PHOSPHO-N-ACETYLMURAMYL-PENTAPEPTIDE TRANSFERASE IN PEPTIDOGLYCAN SYNTHESIS OF ESCHERICHIA-COLI Y-10 [J].

KIMURA, K ;

MIYATA, N ;

KAWANISHI, G ;

KAMIO, Y ;

IZAKI, K ;

ISONO, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (07) :1811-1815

[10] SYNTHESIS OF THE LIPOSIDOMYCIN DIAZEPANONE [J].

KNAPP, S ;

NANDAN, S ;

RESNICK, L .

TETRAHEDRON LETTERS, 1992, 33 (38) :5485-5486