Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction

Eric M. Woerly, Jahnabi Roy, Martin D. Burke

Research output: Contribution to journalArticlepeer-review

Abstract

The inherent modularity of polypeptides, oligonucleotides and oligosaccharides has been harnessed to achieve generalized synthesis platforms. Importantly, like these other targets, most small-molecule natural products are biosynthesized via iterative coupling of bifunctional building blocks. This suggests that many small molecules also possess inherent modularity commensurate with systematic building block-based construction. Supporting this hypothesis, here we report that the polyene motifs found in >75% of all known polyene natural products can be synthesized using just 12 building blocks and one coupling reaction. Using the same general retrosynthetic algorithm and reaction conditions, this platform enabled both the synthesis of a wide range of polyene frameworks that covered all of this natural-product chemical space and the first total syntheses of the polyene natural products asnipyrone B, physarigin A and neurosporaxanthin 2-D-glucopyranoside. Collectively, these results suggest the potential for a more generalized approach to making small molecules in the laboratory.

Original languageEnglish (US)
Pages (from-to)484-491
Number of pages8
JournalNature Chemistry
Volume6
Issue number6
DOIs
StatePublished - Jun 2014

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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