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
收藏
页码：55 / 57
页数：3
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