A new and efficient chemoenzymatic access to both enantiomers of 4-hydroxycyclopent-2-en-1-one

被引：18

作者：

Demir, AS ^{[1
]}

Sesenoglu, O ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(02)00168-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A chemoenzymatic synthesis of both enantiomers of pharmacologically interesting 4-hydroxycyclopent-2-en-1-one in three steps starting from 3-methoxycyclopent-2-en-1-one is described. Manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclopent-2-en-1-one in high enantiomeric excess. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：667 / 670

页数：4

共 32 条

[1] SYNTHESIS OF VERSATILE INTERMEDIATES FOR CYCLOPENTANOID NATURAL-PRODUCTS VIA ENANTIOSELECTIVE DEPROTONATION OF SUBSTITUTED CYCLOPENTENE OXIDE [J].

BHUNIYA, D ;

GUPTA, AD ;

SINGH, VK .

TETRAHEDRON LETTERS, 1995, 36 (16) :2847-2850

[2] Lewis acid catalyzed acylation reactions: scope and limitations [J].

Chandra, KL ;

Saravanan, P ;

Singh, RK ;

Singh, VK .

TETRAHEDRON, 2002, 58 (07) :1369-1374

[3] SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS [J].

COLLINS, PW ;

DJURIC, SW .

CHEMICAL REVIEWS, 1993, 93 (04) :1533-1564

[4] The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol [J].

Curran, TT ;

Hay, DA ;

Koegel, CP ;

Evans, JC .

TETRAHEDRON, 1997, 53 (06) :1983-2004

[5]

DEMIR AS, 1990, SYNTHESIS-STUTTGART, P1119

[6]

DEMIR AS, 1992, SYNTHESIS-STUTTGART, P235

[7] Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones [J].

Demir, AS ;

Hamamci, H ;

Sesenoglu, O ;

Aydogan, F ;

Capanoglu, D ;

Neslihanoglu, R .

TETRAHEDRON-ASYMMETRY, 2001, 12 (13) :1953-1956

[8] Butenolide annelation using a manganese(III) oxidation.: A synthesis of 4-arylfuran-2(5H)-ones [J].

Demir, AS ;

Camkerten, N ;

Gercek, Z ;

Duygu, N ;

Reis, O ;

Arikan, E .

TETRAHEDRON, 1999, 55 (08) :2441-2448

[9] OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID [J].

DEMIR, AS ;

CAMKERTEN, N ;

AKGUN, H ;

TANYELI, C ;

MAHASNEH, AS ;

WATT, DS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2279-2289

[10]

DEMIR AS, 2001, J CHEM SOC P1, V22, P3042

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