Highly stereoselective total synthesis of fully hydroxy-protected mycolactones A and B and their stereoisomerization upon deprotection

  • Wang G
  • Yin N
  • Negishi E
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Unprecedentedly efficient and highly (≥98 %) stereoselective syntheses of mycolactones A and B side chains relied heavily on Pd-catalyzed alkenylation (Negishi version) and were completed in 11 longest linear steps from ethyl (S)-3-hydroxybutyrate in 12% and 11% overall yield, respectively, roughly corresponding to an average of 82% yield per step. The synthesis of mycolactone core was realized by using Pd-catalyzed alkenyl-allyl coupling and an epoxide-opening reaction with a trialkylalkenylaluminate as key steps. Fully hydroxy-protected mycolactones A and B of ≥98% isomeric purity were synthesized successfully for the first time. However, unexpected 4:3-5:4 inseparable mixtures of mycolactones A and B were obtained upon deprotection.

Author-supplied keywords

  • Negishi coupling
  • cross-coupling
  • mycolactones
  • natural products
  • total synthesis

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  • Guangwei Wang

  • Ning Yin

  • Ei Ichi Negishi

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