Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation

  • J Am Chem Soc. 2016 Nov 2;138(43):14246-14249. doi: 10.1021/jacs.6b10645.
Inji Shin   #  1 ,  Suckchang Hong   #  1 ,  Michael J Krische  1
Affiliations
  • 1. University of Texas at Austin, Department of Chemistry, Austin, TX 78712, USA.
  • # Contributed equally.
PMID: 27779393 DOI: 10.1021/jacs.6b10645
Abstract

Diverse hydrogen-mediated C-C couplings enable construction of the actin-binding marine polyketide swinholide A in only 15 steps (longest linear sequence), roughly half the steps required in two prior total syntheses. The redox-economy, chemo- and stereoselectivity embodied by this new class of C-C couplings are shown to evoke a step-change in efficiency.

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