Acyloins from Morita-Baylis-Hillman adducts: an alternative approach to the racemic total synthesis of bupropion

被引：30

作者：

Amarante, Giovanni W. ^{[1
]}

Rezende, Patricia ^{[1
]}

Cavallaro, Mayra ^{[1
]}

Coelho, Fernando ^{[1
]}

机构：

[1] Univ Estadual Campinas, IQ, DQO, Lab Synth Nat Prod & Drugs, BR-13084971 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 23期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/j.tetlet.2008.04.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this Letter, we describe an easy and straightforward strategy for the preparation of acyloins (alpha-hydroxyketones) from Morita-Baylis-Hillman adducts.. based on a Curtius rearrangement. Different acyloins were obtained with good overall yield (>40% for three steps). To exemplify the synthetic usefulness of this strategy, total synthesis of (+/-)-bupropion, a dopamine, and nor-epinefrine reuptake inhibitor has been accomplished in eight steps with an overall yield of 25%. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3744 / 3748

页数：5

共 53 条

[1] Ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes:: an expeditious diastereoselective approach for the preparation of α,β-dihydroxy-esters
Abella, Carlos A. M.
Rezende, Patricia
de Souza, Michele F. Lino
Coelho, Fernando
[J]. TETRAHEDRON LETTERS, 2008, 49 (01) : 145 - 148
[2] Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis
Aggarwal, VK
Fulford, SY
Lloyd-Jones, GC
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) : 1706 - 1708
[3] Piperonal as electrophile in the Baylis-Hillman reaction.: A synthesis of hydroxy-β-piperonyl-γ-butyrolactone derivative
Almeida, WP
Coelho, F
[J]. TETRAHEDRON LETTERS, 1998, 39 (47) : 8609 - 8612
[4] ARCAMONE F, 1985, CANCER RES, V45, P5895
[5] Recent advances in the Baylis-Hillman reaction and applications
Basavaiah, D
Rao, AJ
Satyanarayana, T
[J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
[6] Stereospecific formation of R-aromatic acyloins by Zymomonas mobilis pyruvate decarboxylase
Bornemann, S
Crout, DHG
Dalton, H
Kren, V
Lobell, M
Dean, G
Thomson, N
Turner, MM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (05): : 425 - 430
[7] Christoffers J, 2003, EUR J ORG CHEM, V2003, P425
[8] Ultrasound in Baylis-Hillman reactions with aliphatic and aromatic aldehydes: scope and limitations
Coelho, F
Almeida, WP
Veronese, D
Mateus, CR
Lopes, ECS
Rossi, RC
Silveira, GPC
Pavam, CH
[J]. TETRAHEDRON, 2002, 58 (37) : 7437 - 7447
[9] An approach to oxazolidin-2-ones from the Baylis-Hillman adducts. Formal synthesis of a chloramphenicol derivative
Coelho, F
Rossi, RC
[J]. TETRAHEDRON LETTERS, 2002, 43 (15) : 2797 - 2800
[10] The Baylis-Hillman reaction: A strategy for the preparation of multi-functionalised intermediates for organic synthesis.
Coelho, F
Almeida, WP
[J]. QUIMICA NOVA, 2000, 23 (01): : 98 - 101

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