Three synthetic routes from the commercially available methyl (2S)-3-hydroxy-2-methylpropionate (>99% purity) to  �-D-mannosyl phosphomycoketide (C32-MPM)  were developed. Method A using Julia-Kocienski couplings and platinum-catalyzed hydrogenations afforded the C32 mycoketide  with ~80% optical purity. Methods B and C using Julia-Kocienski couplings and diimide reduction gave enantiopure C32 mycoketide  in high yield. The enantiopure C32  mycoketide  from methods B and C was further converted to the C32-MPM  and the C32-MPM  could be as an auxillary for the CD1c cystallization.  

Total synthesis of enantiomeric pure β-D-mannosyl phosphomycoketide   (C<sub>32</sub>-MPM): A natural product from mycobacterium tuberculosis

243rd National Meeting (2012)

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Total synthesis of enantiomeric pure β-D-mannosyl phosphomycoketide (C32-MPM): A natural product from mycobacterium tuberculosis

Total synthesis of enantiomeric pure β-D-mannosyl phosphomycoketide (C₃₂-MPM): A natural product from mycobacterium tuberculosis