Equilibration in bicyclic pyroglutamates by ring opening-reclosure

被引：11

作者：

Moloney, Mark G. ^{[1
]}

Yaqoob, Muhammad ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 43期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2008.08.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure bicyclic tetramates, readily obtained by Dieckmann ring closure on oxazolidine-derived templates, can be further converted to hydroxypyroglutamates by kinetically controlled nucleophilic additions, and some of these products are capable of equilibration via a facile retro-aldol/aldol reclosure. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6202 / 6204

页数：3

共 9 条

[1] Diastereocontrolled synthesis of hydroxylated lactams [J].

Andrews, MD ;

Brewster, AG ;

Moloney, MG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (01) :80-90

[2]

Andrews MD, 1996, SYNLETT, P612

[3] Regioselective Dieckmann cyclisations leading to enantiopure highly functionalised tetramic acid derivatives [J].

Andrews, MD ;

Brewster, AG ;

Crapnell, KM ;

Ibbett, AJ ;

Jones, T ;

Moloney, MG ;

Prout, K ;

Watkin, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02) :223-235

[4] Efficient enantioselective synthesis of tetramic acids and lactams from threonine [J].

Anwar, Muhammad ;

Moloney, Mark G. .

TETRAHEDRON LETTERS, 2007, 48 (41) :7259-7262

[5] 20S proteasome and its inhibitors: Crystallographic knowledge for drug development [J].

Borissenko, Ljudmila ;

Groll, Michael .

CHEMICAL REVIEWS, 2007, 107 (03) :687-717

[6]

Moloney Mark G, 2004, Curr Drug Discov Technol, V1, P181, DOI 10.2174/1570163043334974

[7] Stereoselective cyanosilylation reactions in hindered cyclic ketones [J].

Moloney, MG ;

Yaqoob, M .

SYNLETT, 2004, (09) :1631-1633

[8] Self-regeneration of stereocenters (SRS) - Applications, limitations, and abandonment of a synthetic principle [J].

Seebach, D ;

Sting, AR ;

Hoffmann, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2708-2748

[9] Cinnabaramides A-G:: Analogues of lactacystin and salinosporamide from a terrestrial streptomycete [J].

Stadler, Marc ;

Bitzer, Jens ;

Mayer-Bartschmid, Anke ;

Mueller, Hartwig ;

Benet-Buchholz, Jordi ;

Gantner, Florian ;

Tichy, Hans-Volker ;

Reinemer, Peter ;

Bacon, Kevin B. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (02) :246-252

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