Concise synthesis of bicyclic pyridinol antioxidants

Jun Lu; Xiaoqing Cai; Sidney Hecht

doi:10.1021/ol102217c

Concise synthesis of bicyclic pyridinol antioxidants

Jun Lu, Xiaoqing Cai, Sidney Hecht

Research output: Contribution to journal › Article › peer-review

24 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 language	English (US)
Pages (from-to)	5189-5191
Number of pages	3
Journal	Organic Letters
Volume	12
Issue number	22
DOIs	https://doi.org/10.1021/ol102217c
State	Published - Nov 19 2010

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102217c

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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.",

author = "Jun Lu and Xiaoqing Cai and Sidney Hecht",

year = "2010",

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T1 - Concise synthesis of bicyclic pyridinol antioxidants

AU - Lu, Jun

AU - Cai, Xiaoqing

AU - Hecht, Sidney

PY - 2010/11/19

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N2 - 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.

AB - 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.

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JO - Organic Letters

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Concise synthesis of bicyclic pyridinol antioxidants

Abstract

ASJC Scopus subject areas

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