Biomimetic Total Synthesis of Santalin Y

Sebastian Strych, Guillaume Journot, Ryan P. Pemberton, Selina C. Wang, Dean J. Tantillo, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

A biomimetic total synthesis of santalin Y, a structurally complex but racemic natural product, is described. The key step is proposed to be a (3+2) cycloaddition of a benzylstyrene to a "vinylogous oxidopyrylium", which is followed by an intramolecular Friedel-Crafts reaction. This cascade generates the unique oxafenestrane framework of the target molecule and sets its five stereocenters in one operation. Our work provides rapid access to santalin Y and clarifies its biosynthetic relationship with other colorants isolated from red sandalwood.

Original languageEnglish (US)
Pages (from-to)5079-5083
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number17
DOIs
StatePublished - Apr 20 2015

Keywords

  • biomimetic synthesis
  • dipolar cycloaddition
  • polyphenols
  • racemic natural products
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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