The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal

Joshua J. Day, Ryan M. McFadden, Scott C. Virgil, Helene Kolding, Jennifer L. Alleva, Brian M. Stoltz

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Ring a ding: The first catalytic enantioselective total synthesis of the meroterpenoid natural product (+)-liphagal is disclosed. The approach showcases a variety of technology including enantioselective enolate alkylation, a photochemical alkyne-alkene [2+2] reaction, microwaveassisted metal catalysis, and an intramolecular aryne capture cyclization reaction. Pivotal to the successful completion of the synthesis was a sequence involving ring expansion from a [6-5-4]
tricycle to a [6-7] bicyclic core followed by stereoselective hydrogenation of a sterically occluded tri-substituted olefin to establish the trans homodecalin system found in the natural product
Original languageEnglish
JournalAngewandte Chemie International Edition
Volume50
Issue number30
Pages (from-to)6814-6818
ISSN1433-7851
DOIs
Publication statusPublished - 2011

Keywords

  • Total synthesis
  • Terpenoids
  • Arynes
  • Asymmetric catalysis
  • Palladium
  • Rearrangement

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