SYNTHESIS OF SHIKIMIC ACID AND ITS PHOSPHONATE ANALOG VIA KNOEVENAGEL CONDENSATION

被引：24

作者：

MIRZA, S

HARVEY, J

机构：

[1] Central Research Laboratories, CIBA-GEIGY Ltd.

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)79876-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Knoevenagel condensation and intramolecular olefination have been successfully exploited in a novel synthesis of shikimic acid 1 and its phosphonate analogue 2 from D-lyxose 5-aldehyde 7.

引用

页码：4111 / 4114

页数：4

共 9 条

[1]

[Anonymous], 1977, WILEY ONLINE LIB

[2] NUCLEOPHILIC DISPLACEMENT REACTIONS IN CARBOHYDRATES .V. REACTION OF 2,3-O-ISOPROPYLIDENE-5-O-METHYLSULPHONYL-D-LYXOFURANOSE WITH SODIUM METHOXIDE - ALDEHYDE-GROUP PARTICIPATION [J].

BRIMACOM.JS ;

HUNEDY, F ;

TUCKER, LCN .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (12) :1381-&

[3] AN ENTRY TO CHIRAL CYCLOHEXENES FROM CARBOHYDRATES - A SHORT, EFFICIENT, AND ENANTIOSPECIFIC SYNTHESIS OF (-)-SHIKIMIC ACID FROM D-MANNOSE [J].

FLEET, GWJ ;

SHING, TKM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (15) :849-850

[4] ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE [J].

FLEET, GWJ ;

SHING, TKM ;

WARR, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :905-908

[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]

Haslam E., 1974, SHIKIMATE PATHWAY

[7] KNOEVENAGEL CONDENSATIONS WITH TICL4 BASE .4. REACTIONS OF ALDEHYDES AND KETONES WITH PHOSPHONOACETIC ESTER AND METHYLENEDIPHOSPHONATES [J].

LEHNERT, W .

TETRAHEDRON, 1974, 30 (02) :301-305

[8] DEOXY-NITROSUGARS .7. SYNTHESIS OF METHYL SHIKIMATE AND OF DIETHYL PHOSPHASHIKIMATE FROM D-RIBOSE [J].

MIRZA, S ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1984, 67 (06) :1562-1567

[9] TITANIUM-MEDIATED STEREOSELECTIVE KNOEVENAGEL CONDENSATION OF ETHYL (DIETHOXYPHOSPHORYL)ACETATE WITH ALDEHYDES [J].

REETZ, MT ;

PETER, R ;

VONITZSTEIN, M .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (01) :121-122

← 1 →