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A Chiron Approach to the Total Synthesis of (-)-Juglomycin A, (+)-Kalafungin, (+)-Frenolicin B, and (+)-Deoxyfrenolicin

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Title A Chiron Approach to the Total Synthesis of (-)-Juglomycin A, (+)-Kalafungin, (+)-Frenolicin B, and (+)-Deoxyfrenolicin
 
Creator FERNANDES, RA
CHAVAN, VP
MULAY, SV
MANCHOJU, A
 
Subject NATURALLY-OCCURRING QUINONES
PICTET-SPENGLER CYCLIZATION
CHROMIUM-CARBENE COMPLEXES
FRENOLICIN-B
EFFICIENT SYNTHESIS
FORMAL SYNTHESIS
PYRANONAPHTHOQUINONE ANTIBIOTICS
ASYMMETRIC DIHYDROXYLATION
NAPHTHOQUINONE ANTIBIOTICS
RACEMIC FRENOLICIN
 
Description A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, D-glucono-delta-lactone, Dotz benzannulation, oxa-Pictet-Spengler reaction, and H2SO4-mediated epimerization.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-16T14:07:51Z
2014-10-16T14:07:51Z
2012
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 77(22)10455-10460
http://dx.doi.org/10.1021/jo3019939
http://dspace.library.iitb.ac.in/jspui/handle/100/15744
 
Language en