Affordable Access

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

Authors
  • FERNANDES, RA
  • KATTANGURU, P
Publication Date
Jan 01, 2013
Source
DSpace at IIT Bombay
Keywords
License
Unknown
External links

Abstract

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.

Report this publication

Statistics

Seen <100 times