A formal synthesis of (+)-lactacystin from 4-hydroxyproline

被引：7

作者：

Mycock, David K. ^{[1
]}

Glossop, Paul A. ^{[2
]}

Lewis, William ^{[1
]}

Hayes, Christopher J. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

(+)-Lactacystin; trans-Hydroxyproline; Enolate acylation; Diastereoselective; Quaternary stereogenic centre; LACTACYSTIN BETA-LACTONE; ENANTIOSELECTIVE TOTAL SYNTHESES; ETHYNYL SUBSTITUTED SERINE; PROTEASOME INHIBITOR; RADICAL CYCLIZATION; D-GLUCOSE; DERIVATIVES; INTERMEDIATE; OMURALIDE; EFFICIENT;

D O I：

10.1016/j.tetlet.2012.10.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal synthesis of (+)-lactacystin has been completed from trans-4-hydroxyproline, using a diastereoselective enolate acylation reaction as a key step. Diastereoselectivity was seen to vary as a function of the steric bulk of the C4-O-protecting group, and contrary to expectations, the best diastereoselectivities were obtained when the small methyl carbonate protecting group was used. The formal synthesis was then completed by intercepting Shibasaki's route via methyl carbonate deprotection, dehydration, 3-pyrroline to 3-pyrrolinone oxidation, hydrogenation and N-CO2Me deprotection. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：55 / 57

页数：3

共 50 条

[21] IMPROVED METHOD FOR THE EVALUATION OF 3-HYDROXYPROLINE AND 4-HYDROXYPROLINE IN THE URINE
BELLON, G
BISKER, A
MAQUART, FX
THOANES, H
BOREL, JP
JOURNAL OF CHROMATOGRAPHY, 1982, 230 (02): : 420 - 426
[22] Stereoselective separation of 4-hydroxyproline by electrokinetic chromatography
Bernardo-Bermejo, Samuel
Adamez-Rodriguez, Sandra
Sanchez-Lopez, Elena
Castro-Puyana, Maria
Marina, Maria Luisa
MICROCHEMICAL JOURNAL, 2023, 185
[23] Decarboxylative formation of N-alkyl pyrroles from 4-hydroxyproline
Deb, Indubhusan
Coiro, Daniel J.
Seidel, Daniel
CHEMICAL COMMUNICATIONS, 2011, 47 (22) : 6473 - 6475
[24] Stereochemistry of 4-hydroxyproline affects the conformation of conopeptides
Xu, Jia
Wang, Yanli
Zhang, Bingbing
Wang, Baohuai
Du, Weihong
CHEMICAL COMMUNICATIONS, 2010, 46 (30) : 5467 - 5469
[25] SUBSTRATE ACTIVITY OF 3-HYDROXYPROLINE ISOMERS FOR ENZYMES ACTIVE WITH 4-HYDROXYPROLINE
ADAMS, E
GOLDSTONE, A
SINGH, RMM
ROSSO, G
BIOCHIMICA ET BIOPHYSICA ACTA, 1964, 89 (01) : 164 - &
[26] SEPARATION OF PROLYL 3-HYDROXYLASE AND 4-HYDROXYLASE ACTIVITIES AND 4-HYDROXYPROLINE REQUIREMENT FOR SYNTHESIS OF 3-HYDROXYPROLINE
TRYGGVASON, K
RISTELI, J
KIVIRIKKO, KI
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1977, 76 (02) : 275 - 281
[27] Development of 4-hydroxyproline ligation for coupling of peptide fragments
Ha, Khanh
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
[28] LIQUID-CHROMATOGRAPHIC DETERMINATION OF 4-HYDROXYPROLINE IN URINE
HUGHES, H
HAGEN, L
SUTTON, RAL
CLINICAL CHEMISTRY, 1986, 32 (06) : 1002 - 1004
[29] A tricyclic template derived from (2S,4R)-4-hydroxyproline for the synthesis of protein loop mimetics
Beeli, R
Steger, M
Linden, A
Robinson, JA
HELVETICA CHIMICA ACTA, 1996, 79 (08) : 2235 - 2248
[30] ON THE ROLE OF 4-HYDROXYPROLINE IN PHYLETIC CHANGE OF COLLAGEN THERMOSTABILITY
BURJANADZE, TV
BIOFIZIKA, 1991, 36 (05): : 778 - 779

← 1 2 3 4 5 →