Step‐Economic and Protecting‐Group‐Free Total Synthesis of (+)‐Cardiobutanolide. Issue 1 (13th November 2012)

• Record Type: Journal Article
• Authors: Fernandes, Rodney A.; Kattanguru, Pullaiah
• Is Part Of: Asian journal of organic chemistry. Volume 2:Issue 1(2013:Jan.)
• Page Start: 74
• Page End: 84
• Publication Date: 2012-11-13
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201200130
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A short protecting‐group‐free synthesis of (+)‐cardiobutanolide is reported. We have modified a one‐pot conversion of <sc>D</sc>‐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 <italic>N</italic>‐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 <sc>D</sc>‐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.</p> </abstract>