Late??Stage β??Epimerization. A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)??Murolic Acid

…, PH Patil, AK Chowdhury

Index: Fernandes, Rodney A.; Patil, Pradnya H.; Chowdhury, Asim K. European Journal of Organic Chemistry, 2014 , vol. 2014, # 1 p. 237 - 243

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Citation Number: 2

Abstract

Abstract The first total synthesis of (+)-murolic acid is accomplished in 17 steps from ester 9 in 14.8% overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson–Claisen rearrangement and α-methylenation using Stiles reagent. A beneficial late stage β-epimerization reverted a stereodivergent relay to a stereoconvergent completion of an efficient synthesis of (+)-murolic acid.