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Total Synthesis of Both Spiroketal Diastereomers of the Reported Structure of Cephalosporolide H

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Title Total Synthesis of Both Spiroketal Diastereomers of the Reported Structure of Cephalosporolide H
 
Creator FERNANDES, RA
HALLE, MB
 
Subject asymmetric dihydroxylation
cephalosporolides
cross metathesis
Keck's allylation
spiroketalization
OLEFIN CROSS-METATHESIS
MARINE-DERIVED FUNGUS
CATALYTIC ASYMMETRIC ALLYLATION
PENICILLIUM-SP
LACTONES
ALDEHYDES
SPONGE
WATER
 
Description A total synthesis of both spiroketal diastereomers of the reported structure of cephalosporolide H is accomplished in 12 steps and 9% overall yield. The key steps involve Keck's allylation, cross metathesis (to get the desired beta,gamma-unsaturated ester), Sharpless asymmetric dihydroxylation (to install the eta-hydroxy-gamma-lactone moiety), and spiroketalization to access both spiroketal diastereomers of the reported structure of the natural product.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-16T14:06:51Z
2014-10-16T14:06:51Z
2013
 
Type Article
 
Identifier ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2(7)593-599
2193-5807
2193-5815
http://dx.doi.org/10.1002/ajoc.201300067
http://dspace.library.iitb.ac.in/jspui/handle/100/15742
 
Language en