A short and efficient synthesis of (-)-7-methylomuralide, a potent proteasome inhibitor.

J Am Chem Soc

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Published: April 2009

AI Article Synopsis

  • Short and efficient methods for synthesizing both (+/-)-7-methylomuralide and (-)-7-methylomuralide have been created.
  • Three successive tandem reactions are used to build the required carbon structure and stereochemistry of the target molecule, making the synthesis process much simpler.
  • A chiral directing group is utilized to manage the stereochemistry in a crucial aldol reaction step.

Article Abstract

Short, practical, and scalable syntheses of (+/-)-7-methylomuralide and (-)-7-methylomuralide have been developed. Three consecutive tandem reaction pairs establish all of the carbons and the stereochemistry of the target molecule, vastly simplifying the synthetic scheme from N-trichloroethoxycarbonyl glycine. The chiral directing group controls the absolute stereochemistry of the key aldol reaction.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2714661PMC
http://dx.doi.org/10.1021/ja901400qDOI Listing

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