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Step-Economic and Protecting-Group-Free Total Synthesis of (+)-Cardiobutanolide

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Title Step-Economic and Protecting-Group-Free Total Synthesis of (+)-Cardiobutanolide
 
Creator FERNANDES, RA
KATTANGURU, P
 
Subject asymmetric dihydroxylation
cardiobutanolide
cross-metathesis
natural products
styryllactones
STEREOSELECTIVE TOTAL-SYNTHESIS
OLEFIN CROSS-METATHESIS
ASYMMETRIC DIHYDROXYLATION
ANNONACEAE
ALKALOIDS
(+)-GONIOFUFURONE
STYRYLLACTONE
DERIVATIVES
 
Description A short protecting-group-free synthesis of (+)-cardiobutanolide is reported. We have modified a one-pot conversion of D-glucono-delta-lactone into the building block beta-hydroxy-gamma-lactone. A series of cross-metathesis reactions and dihydroxylations either under the Sharpless conditions or achiral 4-methylmorpholine N-oxide (NMO) conditions were used to synthesize (+)-cardiobutanolide and its various diastereomers. In this endeavour, we have achieved a step-economic and protecting-group-free synthesis of (+)-cardiobutanolide in 22.4% overall yield from d-glucono-delta-lactone. A cross-metathesis reaction that is compatible with hydroxy groups and a substrate controlled Upjohn dihydroxylation reaction are key steps in the synthesis. The synthesis is highly efficient and competitive with previous reports.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-16T14:03:49Z
2014-10-16T14:03:49Z
2013
 
Type Article
 
Identifier ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2(1)74-84
2193-5807
2193-5815
http://dx.doi.org/10.1002/ajoc.201200130
http://dspace.library.iitb.ac.in/jspui/handle/100/15736
 
Language en