Concise synthesis of bicyclic pyridinol antioxidants

Jun Lu, Xiaoqing Cai, Sidney Hecht

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

The recently reported bicyclic pyridinols 1 and 2 are highly effective antioxidants exhibiting 88- and 28-fold greater potency, respectively, than α-tocopherol when assayed for their ability to suppress the autoxidation of methyl linoleate. Described herein is a short, economical, and scalable strategy for the synthesis of this novel group of antioxidants, as well as analogues 3-6. Key reactions involved the cyclocondensation reaction of lactam acetals with enaminone 7 and selective functionalizaton of the heterocyclic systems.

Original languageEnglish (US)
Pages (from-to)5189-5191
Number of pages3
JournalOrganic Letters
Volume12
Issue number22
DOIs
StatePublished - Nov 19 2010

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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