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Stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3

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Title Stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3
 
Creator FERNANDES, RA
INGLE, AB
CHAVAN, VP
 
Subject CHROMIUM-CARBENE COMPLEXES
DERMOCYBE CARDINALIS
ALKYNE CYCLOADDITION
(+)-NOCARDIONE B
FORMAL SYNTHESIS
VENTILOQUINONE-L
(+)-ALLO-ELEUTHERIN
(+)-ELEUTHERIN
ANTIBIOTICS
PIGMENTS
 
Description A stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3 has been described. The synthesis is completed in 7 steps with 10.5% and 13% overall yields for (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L respectively. The key steps involve Dotz benzannulation of carbene 5 with alkyne 6 to give a substituted naphthalene moiety and oxa-Pictet-Spengler reaction to install the 1,3-dimethylpyran moiety.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-16T14:04:49Z
2014-10-16T14:04:49Z
2012
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 10(22)4462-4466
http://dx.doi.org/10.1039/c2ob25453k
http://dspace.library.iitb.ac.in/jspui/handle/100/15738
 
Language en