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Step‐Economic and Protecting‐Group‐Free Total Synthesis of (+)‐Cardiobutanolide
Author(s) -
Fernandes Rodney A.,
Kattanguru Pullaiah
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200130
Subject(s) - chemistry , protecting group , metathesis , yield (engineering) , lactone , dihydroxylation , total synthesis , group (periodic table) , sharpless asymmetric dihydroxylation , diastereomer , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , alkyl , materials science , metallurgy , polymerization , polymer
Abstract A short protecting‐group‐free synthesis of (+)‐cardiobutanolide is reported. We have modified a one‐pot conversion of D ‐glucono‐δ‐lactone into the building block β‐hydroxy‐γ‐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‐δ‐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.