A new synthesis of dehydroluciferin [2-(6'-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid] from 1,4-benzoquinone
Articolo
Data di Pubblicazione:
2013
Citazione:
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.
Abstract:
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).
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
dehydroluciferin; firefly luciferase; natural products; heterocycles; total synthesis
Elenco autori:
P. Ciuffreda, S. Casati, G. Meroni, E. Santaniello
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