Total Synthesis of the Diterpene Waihoensene

Abstract A racemic and scalable enantioselective total synthesis of (+)‐waihoensene was accomplished. (+)‐Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all‐cis‐fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson–Khand reaction, a diastereoselective α‐alkylation, and a diastereoselective 1,4‐addition reaction. Enantioselectivity was introduced at an early stage, by an asymmetric palladium catalyzed decarboxylative allylation reaction on gram scale.

• Publication year

  2020

• Venue

  Angewandte Chemie

• Publication date

  2020-10-25

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.202011298PMID 33103334PMCID 7898921
• 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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