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

[21]

OTSUKA S, 1991, SYNTHESIS-STUTTGART, P665

[22] SYNTHESIS OF DEOXY SUGARS - DEOXYGENATION BY TREATMENT WITH N,N'-THIOCARBONYLDIIMIDAZOLE-TRI-NORMAL-BUTYLSTANNANE [J].

RASMUSSEN, JR ;

SLINGER, CJ ;

KORDISH, RJ ;

NEWMANEVANS, DD .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4843-4846

[23] A STEREOSPECIFIC SYNTHESIS OF DL-QUINIC ACID [J].

SMISSMAN, EE ;

OXMAN, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2184-&

[24] ENANTIOSELECTIVE SYNTHESIS OF (1S,3S,5R)-1-ACETOXY-5-BENZYL-OXYCYCLOHEXAN-3-OL AND ITS APPLICATION TO THE SYNTHESIS OF COMPACTIN LACTONE MOIETY AND QUINIC ACID [J].

SUEMUNE, H ;

MATSUNO, K ;

UCHIDA, M ;

SAKAI, K .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :297-306

[25] STEREOSPECIFIC SYNTHESIS OF (+-)-QUINIC ACID [J].

WOLINSKY, J ;

NOVAK, R ;

VASILEFF, R .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (12) :3596-&

[26]

1996, MERCK INDEX, V12, P8243

← 1 2 3 →