Novel asymmetric syntheses of (-)-malyngolide and (+)-epi-malyngolide

Article abstract of DOI:10.1016/0040-4020(96)00236-0

The diastereo- and enantioselective synthesis of (-)-malyngolide [(S,R)-1], an antibiotic against Mycobacterium smegmatis and Streptococcus pyogenes, using the asymmetric Carroll rearrangement as key step is described. Furthermore, the diastereo- and enantioselective synthesis by double α,α'-alkylation using SAMP/RAMP hydrazone methodology affords the diastereomer (+)-epi-malyngolide [(S,S)-1].