Chemo- and biocatalytic strategies to obtain phenylisoserine, a lateral chain of Taxol by asymmetric reduction

被引：18

作者：

Rimoldi, Isabella ^{[1
,2
]}

Pellizzoni, Michela ^{[4
]}

Facchetti, Giorgio ^{[1
,2
]}

Molinari, Francesco ^{[3
]}

Zerla, Daniele ^{[1
,2
]}

Gandolfi, Raffaella ^{[4
]}

机构：

[1] Univ Milan, Fac Farm, Dipartimento Chim Inorgan Met Organ & Analit L Ma, I-20133 Milan, Italy

[2] Ist CNR ISTM, I-20133 Milan, Italy

[3] Univ Milan, Fac Agr, DISTAM Sez Microbiol Ind, I-20133 Milan, Italy

[4] Univ Milan, Fac Farm, Dipartimento Sci Mol Applicate Biosistemi, Sez Chim Organ A Marchesini, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 24期

关键词：

HIGHLY EFFICIENT CATALYSTS; 1ST TOTAL-SYNTHESIS; C-13; SIDE-CHAIN; ENANTIOSELECTIVE HYDROGENATION; ACID-DERIVATIVES; ALPHA-KETOESTERS; TAXUS-BREVIFOLIA; AMINO-ACIDS; PACIFIC YEW; COMPLEXES;

D O I：

10.1016/j.tetasy.2011.11.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enriched ethyl 3-benzamido-2-hydroxy-3-phenylpropanoate (protected phenylisoserine), the chiral side chain of Taxol, was obtained via asymmetric reduction with transition metal-diphoshine complexes or with whole cells of non-conventional yeasts. Asymmetric hydrogenation was carried out using different approaches: hydrogenation of the tetra-substituted double bond of (E)-1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate 1 with Ir(I)-diphosphine complexes in the presence of TEA, hydrogenation of the carbonyl group of racemic ethyl 3-benzamido-2-oxo-3-phenylpropanoate 2 with Ru(II)-diphoshine complexes in the presence of a Lewis acid and finally a two-step enzymatic transformation of (E)-1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate 1 catalyzed by whole cells of yeasts bearing cell-bound esterases and dehydrogenases. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2110 / 2116

页数：7

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