A concise enantio- and diastereo-controlled synthesis of (-)-quinic acid and (-)-shikimic acid

被引：17

作者：

Hiroya, K ^{[1
]}

Ogasawara, K ^{[1
]}

机构：

[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 18期

关键词：

D O I：

10.1039/a805775c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-Quinic acid and (-)-shikimic acid, both recognized as the key intermediates in the shikimate pathway in plants and microorganisms, have been synthesized concisely in an enantio- and diastereo-controlled manner starting from a synthetic equivalent of (R)-4-hydroxycyclohex-2-enone.

引用

页码：2033 / 2034

页数：2

共 26 条

[1] D-(-)-quinic acid: a chiron store for natural product synthesis [J].

Barco, A ;

Benetti, S ;

DeRisi, C ;

Marchetti, P ;

Pollini, GP ;

Zanirato, V .

TETRAHEDRON-ASYMMETRY, 1997, 8 (21) :3515-3545

[2]

BARTON DHR, 1981, SYNTHESIS-STUTTGART, P743

[3] STEREOSPECIFIC SYNTHESIS OF OPTICALLY PURE QUINIC ACID AND SHIKIMIC ACID FROM D-ARABINOSE [J].

BESTMANN, HJ ;

HEID, HA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (05) :336-&

[4]

Buchi G, 1970, J Am Chem Soc, V92, P999

[5]

CAMPBELL MM, 1993, SYNTHESIS-STUTTGART, P179

[6]

Dewick PM, 1998, NAT PROD REP, V15, P17

[7] 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

[8] DIE TOTALSYNTHESE DER CHINASAURE [J].

GREWE, R ;

LORENZEN, W ;

VINING, L .

CHEMISCHE BERICHTE-RECUEIL, 1954, 87 (06) :793-802

[9]

Haslam E., 1996, PROGR CHEM ORGANIC N, V69, P158

[10] ASYMMETRIZATION OF MESO 1,4-ENEDIOL ETHERS BY ISOMERIZATION WITH A CHIRAL BINAP-RH-I CATALYST [J].

HIROYA, K ;

KURIHARA, Y ;

OGASAWARA, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (20) :2287-2289

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