1403608-20-7Relevant articles and documents
Asymmetric total syntheses of cochliomycin A and zeaenol
Jana, Nandan,Nanda, Samik
, p. 4313 - 4320 (2012/09/22)
The first asymmetric total syntheses of two resorcylic acid lactones (RALs) - cochliomycin A and zeaenol - have been achieved in a divergent way. The main highlight of our strategy involves successful application of stereoselecive Keck allylation and Julia-Kocienski olefination to access an advanced intermediate, by starting from L-tartaric acid as a chiral pool compound. This intermediate is coupled with a trisubstituted benzoic acid to afford a common RCM precursor for both target molecules. Ring-closing metathesis at a late stage, followed by functional group manipulation, yielded the target molecules in an efficient way. Two resorcylic acid lactones (RALs) - cochliomycin A and zeaenol - have been synthesized for the first time by an enantiodivergent route from the common chiral pool compound L-tartaric acid. Copyright