A new synthesis of dehydroluciferin [2-(60-hydroxy-20-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 oxidationecyclization 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 a-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 4-benzoquinone (69% from 6-hydroxybenzothiazole).
A new synthesis of dehydroluciferin [2-(6'-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid] from 1,4-benzoquinone / P. Ciuffreda, S. Casati, G. Meroni, E. Santaniello. - In: TETRAHEDRON. - ISSN 0040-4020. - 69:29(2013 Jul), pp. 5893-5897.
Titolo: | A new synthesis of dehydroluciferin [2-(6'-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid] from 1,4-benzoquinone | |
Autori: | CIUFFREDA, PIERANGELA (Primo) CASATI, SILVANA MARIA (Secondo) MERONI, GIUSEPPE (Penultimo) SANTANIELLO, ENZO (Ultimo) | |
Parole Chiave: | dehydroluciferin; firefly luciferase; natural products; heterocycles; total synthesis | |
Settore Scientifico Disciplinare: | Settore BIO/10 - Biochimica | |
Data di pubblicazione: | lug-2013 | |
Rivista: | ||
Tipologia: | Article (author) | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2013.05.019 | |
Appare nelle tipologie: | 01 - Articolo su periodico |
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