PREPARATION OF NEW QUINIC ACID BORON ESTERS IN APROTIC MEDIA

被引：17

作者：

FLORESPARRA, A

PAREDESTEPOX, C

JOSEPHNATHAN, P

CONTRERAS, R

机构：

[1] Departamento de Química, Mexico

来源：

TETRAHEDRON | 1990年 / 46卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(01)86749-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses, structure and reactivity of several boron derivatives of quinic acid, obtained in aprotic media, show that these boron heterocycles are useful intermediates, since they provide an alternative route to functionalize the quinic acid in a different way as when using dioxolane derivatives. Some new dioxolane derivatives of quinic acid and free quinide, as well as the lactone of quinic acid (6), were prepared in very high yields. The conformations of all new compounds were established from 1H NMR measurements. © 1990.

引用

收藏

页码：4137 / 4148

页数：12

相关论文

共 11 条

[1] CYCLIC BORATES PREPARED FROM SHIKIMIC ACID AND QUINIC ACID AND THEIR METHYL-ESTERS - STRUCTURE AND STABILITY IN AQUEOUS-SOLUTION [J].

DELFOURNE, E ;

VERONIQUE, J ;

GORRICHON, L ;

MUNOZ, A ;

LAMANDE, L .

TETRAHEDRON, 1989, 45 (09) :2605-2614

[2] C-13 AND H-1-NMR INVESTIGATIONS OF QUINIC ACID-DERIVATIVES - COMPLETE SPECTRAL ASSIGNMENT AND ELUCIDATION OF PREFERRED CONFORMATIONS [J].

FLORESPARRA, A ;

GUTIERREZAVELLA, DM ;

CONTRERAS, R ;

KHUONGHUU, F .

MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (06) :544-555

[3] AN APPROACH TO ENTEROCINE SYNTHESIS - ADDITION OF ALPHA-SULFURED CARBANIONS TO QUINIDES [J].

FLORESPARRA, A ;

KHUONGHUU, F .

TETRAHEDRON, 1986, 42 (21) :5925-5930

[4]

FLORESPARRA A, 1985, THESIS U PARIS SUD

[5] SHIKIMATE-DERIVED METABOLITES .4. FROM GLUCOSE TO AROMATICS - RECENT DEVELOPMENTS IN NATURAL-PRODUCTS OF SHIKIMIC ACID PATHWAY [J].

GANEM, B .

TETRAHEDRON, 1978, 34 (23) :3353-3383

[6] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[7]

HASLAM E, 1979, COMPREHENSIVE ORGANI, V5, P1167

[8]

N?th H., 1978, NMR BASIC PRINCIPLES, V14

[9] STRUCTURAL REQUIREMENTS FOR CATALYSIS BY CHORISMATE MUTASE [J].

PAWLAK, JL ;

PADYKULA, RE ;

KRONIS, JD ;

ALEKSEJCZYK, RA ;

BERCHTOLD, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3374-3381

[10] HIGHLY STEREOCONTROLLED SYNTHESIS OF SOME TRIOXYGENATED CYCLOHEXENES - AN ASYMMETRIC TOTAL SYNTHESIS OF (-)-METHYL TRIACETYL-4-EPISHIKIMATE [J].

POSNER, GH ;

WETTLAUFER, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7373-7377