SYNTHESIS OF A CYCLITOL VIA A TANDEM ENZYMATIC ALDOL - INTRAMOLECULAR HORNER-WADSWORTH-EMMONS REACTION

被引:21
作者
GIJSEN, HJM [1 ]
WONG, CH [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)01483-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldol condensation between a phosphonate aldehyde and dihydroxyacetone phosphate catalyzed by fructose 1,6-diphosphate aldolase (EC 4.1.2.13) gives a product which in situ cyclizes via an intramolecular Horner-Wadsworth-Emmans (HWE) olefination to afford a polyhydroxylated cyclopentene. In this one-pot reaction, the HWE reaction takes place in aqueous solution at slightly acidic (pH 6.1-6.8) conditions.
引用
收藏
页码:7057 / 7060
页数:4
相关论文
共 18 条
[11]   AN EFFICIENT MULTIGRAM-SCALE PREPARATION OF DIHYDROXYACETONE PHOSPHATE [J].
JUNG, SH ;
JEONG, JH ;
MILLER, P ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7182-7184
[12]   A (1-]4)-TREHAZOLOID GLUCOSIDASE INHIBITOR WITH AGLYCON SELECTIVITY [J].
KNAPP, S ;
PURANDARE, A ;
RUPITZ, K ;
WITHERS, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7461-7462
[13]   THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].
MARYANOFF, BE ;
REITZ, AB .
CHEMICAL REVIEWS, 1989, 89 (04) :863-927
[14]   PREPARATION OF SUGAR-DERIVED BETA-KETO PHOSPHONATES AND THEIR USE IN THE SYNTHESIS OF HIGHER SUGARS [J].
NARKUNAN, K ;
NAGARAJAN, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6386-6390
[15]   A NEW APPROACH TO CYCLITOLS BASED ON RABBIT MUSCLE ALDOLASE (RAMA) [J].
SCHMID, W ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9670-9671
[16]   STEREOCONTROLLED SYNTHESES OF 6-EPI-TREHAZOLIN AND 6-EPI-TREHALAMINE FROM D-RIBONOLACTONE [J].
SHIOZAKI, M ;
ARAI, M ;
KOBAYASHI, Y ;
KASUYA, A ;
MIYAMOTO, S ;
FURUKAWA, Y ;
TAKAYAMA, T ;
HARUYAMA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4450-4460
[17]   ENZYMES IN ORGANIC-SYNTHESIS - APPLICATION TO THE PROBLEMS OF CARBOHYDRATE-RECOGNITION .1. [J].
WONG, CH ;
HALCOMB, RL ;
ICHIKAWA, Y ;
KAJIMOTO, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (04) :412-432
[18]  
WONG CH, 1994, ENZYMES SYNTHETIC OR, P195