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A concise total synthesis of arizonins B1 and C1

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Title A concise total synthesis of arizonins B1 and C1
 
Creator FERNANDES, RA
MULAY, SV
CHAVAN, VP
 
Subject ENANTIODIVERGENT TOTAL SYNTHESES
PICTET-SPENGLER CYCLIZATION
CHROMIUM CARBENE COMPLEXES
ASYMMETRIC DIHYDROXYLATION
ENANTIOSELECTIVE SYNTHESIS
3C-PROTEASE INHIBITOR
KALAFUNGIN
ANNULATION
THYSANONE
(-)-NANAOMYCIN-D
 
Description A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-16T14:02:48Z
2014-10-16T14:02:48Z
2013
 
Type Article
 
Identifier TETRAHEDRON-ASYMMETRY, 24(24)1548-1555
http://dx.doi.org/10.1016/j.tetasy.2013.10.011
http://dspace.library.iitb.ac.in/jspui/handle/100/15734
 
Language en