Intramolecular sulfur-assisted NaBH4 reduction of esters synthesis of 5-oxo-ETE and 5-oxo-12-HETE

被引：9

作者：

Khanapure, SP

Saha, G

Sivendran, S

Powell, WS

Rokach, J

机构：

[1] Florida Inst Technol, Claude Pepper Inst, Melbourne, FL 32901 USA

[2] Florida Inst Technol, Dept Chem, Melbourne, FL 32901 USA

[3] McGill Univ, Meakins Christie Labs, Montreal, PQ H2X 2P2, Canada

[4] McGill Univ, Dept Med, Montreal, PQ H2X 2P2, Canada

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 30期

基金：

英国医学研究理事会; 美国国家卫生研究院; 美国国家科学基金会;

关键词：

NaBH4; MeOH; 5-oxo-ETE;

D O I：

10.1016/S0040-4039(00)00943-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ester groups are reduced very efficiently in sulfur-containing molecules situated at close proximity to the ester group. We have used this procedure to regioselectively, efficiently and in high yield reduce an ester group in the presence of another ester group further removed from the sulfur atom. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5653 / 5657

页数：5

共 50 条

[41] Phenacyl esters of acetic acid derivatives and their application for the synthesis of 2-oxo-4-phenyl-5-(phenylhydrazono)-2,5-dihydro-furan-3-derivatives
Melnicky, Radek
Kvapil, Lubomir
Slezar, Petr
Grepl, Martin
Hlavac, Jan
Lycka, Antonin
Hradil, Pavel
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1437 - 1443
[42] Synthesis, characterization and assignment of the absolute configuration of 4,4-dimethyl-5-oxo-tetrahydrofuran-3-carboxylic acid and its esters: a combined experimental and theoretical investigation
Coriani, Sonia
Forzato, Cristina
Furlan, Giada
Nitti, Patrizia
Pitacco, Giuliana
Ringholm, Magnus
Ruud, Kenneth
TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1459 - 1467
[43] ACTION OF THIOSEMICARBAZIDE ON OXALACETIC ACID-ESTERS - SYNTHESIS OF 3-THIOXO-5-OXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINES
MAUDET, D
GRANET, R
PIEKARSKI, S
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1975, (11-1): : 2696 - 2702
[44] SYNTHESIS AND INSECTICIDAL AND ACARICIDAL PROPERTIES OF SOME 5-METHOXY-1-METHYL-6-OXO-1H-PYRIDAZIN-4-YL PHOSPHORUS ESTERS .3.
KONECNY, V
VARKONDA, S
VARGOVA, M
PESTICIDE SCIENCE, 1976, 7 (02): : 107 - 114
[45] Synthesis of 4-Aryl-6-oxo-5-cyano-1,6-dihydropyridine-2-carboxylic Acids and Their Methyl Esters by Reacting Methyl Acylpyruvates with Malononitrile and Cyanoacetamide
M. A. Maryasov
N. P. Romashov
V. V. Davydova
O. E. Nasakin
M. P. Osipova
Russian Journal of General Chemistry, 2021, 91 : 947 - 950
[46] Synthesis of 4-substituted-3-hydroxy-5-oxo-10-oxa-4-azatricyclo[5.2.1]dec-3-yl Acetic Acid Ethyl Esters as Norcantharidin Analogues
Sauer, Benjamin
Gilbert, Jayne
Sakoff, Jennette A.
McCluskey, Adam
LETTERS IN DRUG DESIGN & DISCOVERY, 2009, 6 (01) : 1 - 7
[47] SYNTHESIS OF 7-HYDROXY-3-KETO-5-BETA-CHOLAN-24-OIC AND 12-HYDROXY-3-KETO-5-BETA-CHOLAN-24-OIC AND 7,12-DIHYDROXY-3-KETO-5-BETA-CHOLAN-24-OIC ACIDS BY REDUCTION OF 3,7-OXO, 3,12-OXO AND 3,7,12-OXO DERIVATIVES
FANTIN, G
FOGAGNOLO, M
MEDICI, A
PEDRINI, P
COVA, U
STEROIDS, 1993, 58 (11) : 524 - 526
[48] SYNTHESIS AND CHARACTERIZATION OF 2-DIAZO-1-OXO-1,2-DIHYDRONAPHTHALEN-5-SULFONIC ACID-ESTERS OF 2,6-BIS(2-HYDROXY-5-CUMYLBENZYL)-4-CUMYLPHENOL
PASCH, H
JOURNAL FUR PRAKTISCHE CHEMIE, 1987, 329 (06): : 1143 - 1146
[49] Synthesis of 3-oxo-1,4-diazepine-5-carboxamides and 6-(4-oxo-chromen-3-yl)-pyrazinones via sequential Ugi 4CC/Staudinger/intramolecular nucleophilic cyclization and Ugi 4CC/Staudinger/aza-Wittig reactions
Akbarzadeh, Roya
Our, Tayebeh Amanp
Bazgir, Ayoob
TETRAHEDRON, 2014, 70 (43) : 8142 - 8147
[50] PREPARATION OF CHIRAL β-ENAMINO ESTERS FROM METHYL PROPIOLATE: SYNTHESIS OF CHIRAL METHYL 1-SUBSTITUTED 6-OXO-1,4,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATES
Pilotzi, Hugo
Gnecco, Dino
Orea, Maria L.
Juarez, Jorge R.
Aparicio, David M.
Teran, Joel L.
HETEROCYCLES, 2018, 96 (05) : 899 - 905

← 1 2 3 4 5 →