A Concise Total Synthesis of (+)-Waihoensene Guided by Quaternary Center Analysis.

The four contiguous all-carbon quaternary centers of waihoensene, coupled with the absence of any traditional reactive functional groups other than a single alkene, renders it a particularly challenging synthetic target among angular triquinane natural products.  Here, we show that its polycyclic frame can be assembled concisely by using a strategically selected quaternary center to guide the formation of the other three through judiciously selected C-C bond formation reactions.  Those events, which included a unique Conia-ene cyclization and a challenging Pauson-Khand reaction, afforded a 17-step synthesis of the molecule in enantioenriched form.

• Publication year

  2020

• Venue

  Angewandte Chemie

• Publication date

  2020-04-24

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.202004177PMID 32330370PMCID PMC7906115
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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