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A highly diastereoselective oxa-Pictet-Spengler approach to (+)-astropaquinone B and (+)-astropaquinone C and the formation of astropaquinone B dimer

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Title A highly diastereoselective oxa-Pictet-Spengler approach to (+)-astropaquinone B and (+)-astropaquinone C and the formation of astropaquinone B dimer
 
Creator FERNANDES, RA
MULAY, SV
 
Subject 3C-PROTEASE INHIBITOR THYSANONE
CHROMIUM CARBENE COMPLEXES
ENANTIOSELECTIVE SYNTHESIS
PYRANONAPHTHOQUINONE ANTIBIOTICS
STEREOSELECTIVE-SYNTHESIS
(+)-VENTILOQUINONE L
ANNULATION STRATEGY
BIOLOGICAL-ACTIVITY
(+)-NOCARDIONE B
DEOXY ANALOGS
 
Description A concise and highly diastereoselective synthesis of (+)-astropaquinone B and (+)-astropaquinone C is reported. The synthetic strategy is based on an efficient combination of Dotz benzannulation using a chiral alkyne to construct the naphthalene unit and a highly diastereoselective oxa-Pictet-Spengler reaction to install the trans-configured pyran ring as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-16T14:03:18Z
2014-10-16T14:03:18Z
2013
 
Type Article
 
Identifier TETRAHEDRON-ASYMMETRY, 24(20)1281-1285
http://dx.doi.org/10.1016/j.tetasy.2013.09.001
http://dspace.library.iitb.ac.in/jspui/handle/100/15735
 
Language en