A new synthesis of dehydroluciferin [2-(6′-hydroxy-2′-benzothiazolyl)-thiazole-4-carboxylic acid] from 1,4-benzoquinone

被引：9
|
作者：
Ciuffreda, Pierangela [1 ]
Casati, Silvana [1 ]
Meroni, Giuseppe [2 ]
Santaniello, Enzo [2 ]
机构：
[1] Univ Milan, Dipartimento Sci Biomed & Clin L Sacco, I-20157 Milan, Italy
[2] Univ Milan, Dipartimento Sci Salute, I-20142 Milan, Italy
来源：
TETRAHEDRON | 2013年 / 69卷 / 29期
关键词：
Dehydroluciferin; Firefly luciferase; Natural products; Heterocycles; Total synthesis; LUCIFERASE GENE-EXPRESSION; FIREFLY LUCIFERASE; IN-VIVO; LIVING MICE; BIOLUMINESCENCE; PET; BENZOTHIAZOLES; DERIVATIVES; ANALOGS; SPECT;
D O I：
10.1016/j.tet.2013.05.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthesis of dehydroluciferin [2-(6'-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid], the oxidative product of luciferin, has been realized starting from 1,4-benzoquinone. Reaction of this compound with L-cysteine ethyl ester, followed by an oxidation-cyclization step afforded 2-carbethoxy-6-hydroxybenzothiazole that was in situ hydrolyzed and decarboxylated to 6-hydroxybenzothiazole. The tert-butyl(dimethyl)silyl ether of this key intermediate was subjected to alpha-lithiation followed by formylation with DMF, and the resulting aldehyde condensed with L-cysteine ethyl ester. Dehydrogenation of the intermediate thiazolidine followed by deprotection afforded dehydroluciferin in 35% overall yield from 1,4-benzoquinone (69% from 6-hydroxybenzothiazole). (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5893 / 5897
页数：5
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