Concise synthesis of bicyclic pyridinol antioxidants

Jun Lu, Xiaoqing Cai, Sidney Hecht

Research output: Contribution to journalArticle

20 Citations (Scopus)

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

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antioxidants
Antioxidants
tocopherol
Lactams
acetals
Acetals
Tocopherols
synthesis
analogs
methyl linoleate

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Concise synthesis of bicyclic pyridinol antioxidants. / Lu, Jun; Cai, Xiaoqing; Hecht, Sidney.

In: Organic Letters, Vol. 12, No. 22, 19.11.2010, p. 5189-5191.

Research output: Contribution to journalArticle

Lu, Jun ; Cai, Xiaoqing ; Hecht, Sidney. / Concise synthesis of bicyclic pyridinol antioxidants. In: Organic Letters. 2010 ; Vol. 12, No. 22. pp. 5189-5191.
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