Total synthesis of brasoside and littoralisone

Ian K. Mangion, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

174 Scopus citations

Abstract

The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed α-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.

Original languageEnglish (US)
Pages (from-to)3696-3697
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number11
DOIs
StatePublished - Mar 23 2005

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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