APPLICATION OF YEAST-CATALYZED REDUCTIONS TO SYNTHESIS OF (2R,3S)-PHENYLISOSERINE

被引：48

作者：

KEARNS, J ^{[1
]}

KAYSER, MM ^{[1
]}

机构：

[1] UNIV NEW BRUNSWICK,DEPT PHYS SCI,ST JOHN E2L 4L5,NB,CANADA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)76640-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple synthesis of (2R,3S)-phenylisoserine, a precursor of the C-13 side chain of Taxol(R)(paclitaxel), utilising yeast-catalyzed reduction to generate a second chiral centre is reported. This short enantioselective series of transformations can be readily adapted to large scale production of a variety of N-substituted paclitaxel analogues.

引用

页码：2845 / 2848

页数：4

共 50 条

[1] Investigations on the synthesis of (2R,3S)-3-phenylisoserine hydrochloride
Jezierska-Zieba, Magdalena
Kakol, Barbara
Obukowicz, Bozenna
Cybulski, Jacek
Fedorynski, Michal
Szpakiewicz, Miroslawa
PRZEMYSL CHEMICZNY, 2007, 86 (04): : 318 - 323
[2] A study on purification of (2R,3S)-3-phenylisoserine hydrochloride
Kakol, Barbara
Jezierska-Zieba, Magdalena
Szpakiewicz, Miroslawa
Cybulski, Jacek
PRZEMYSL CHEMICZNY, 2009, 88 (11): : 1240 - 1242
[3] (2R,3S)-phenylisoserine hydrochloride - an intermediate product on the route to Paclitaxel
Kakol, B
Jezierska-Zieba, M
Kaminski, J
Obukowicz, B
Beldowicz, M
Szpakiewicz, M
Golinski, J
PRZEMYSL CHEMICZNY, 2002, 81 (12): : 780 - 784
[4] STEREOSPECIFIC PREPARATION OF GLYCIDIC ESTERS FROM 2-CHLORO-3-HYDROXYESTERS - APPLICATION TO THE SYNTHESIS OF (2R,3S)-3-PHENYLISOSERINE
CABON, O
BUISSON, D
LARCHEVEQUE, M
AZERAD, R
TETRAHEDRON-ASYMMETRY, 1995, 6 (09) : 2211 - 2218
[5] Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine
Njogu, Peter M.
Gut, Jiri
Rosenthal, Philip J.
Chibale, Kelly
ACS MEDICINAL CHEMISTRY LETTERS, 2013, 4 (07): : 72 - 76
[6] Enantioselective synthesis of (2R,3S)-(+)-catechin
Jew, S
Lim, D
Bae, S
Kim, H
Kim, J
Lee, J
Park, H
TETRAHEDRON-ASYMMETRY, 2002, 13 (07) : 715 - 720
[7] Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines
Raghavan, S
Tony, KA
TETRAHEDRON LETTERS, 2004, 45 (12) : 2639 - 2641
[8] N-BENZOYL-(2R,3S)-PHENYLISOSERINE METHYL-ESTER - A FACILE AND CONVENIENT SYNTHESIS AND RESOLUTION BY ENTRAINMENT
SRIVASTAVA, RP
ZJAWIONY, JK
PETERSON, JR
MCCHESNEY, JD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 84 - MEDI
[9] N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE METHYL-ESTER - A FACILE AND CONVENIENT SYNTHESIS AND RESOLUTION BY ENTRAINMENT
SRIVASTAVA, RP
ZJAWIONY, JK
PETERSON, JR
MCCHESNEY, JD
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) : 1683 - 1688
[10] A practical stereoselective synthesis of (2R,3S)-alloisoleucine
Portonovo, P
Liang, B
Joullié, MM
TETRAHEDRON-ASYMMETRY, 1999, 10 (08) : 1451 - 1455

← 1 2 3 4 5 →