DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism

Ye Ding; Zhangjian Huang; Jian Yin; Yisheng Lai; Shibo Zhang; Zhiguo Zhang; Lei Fang; Sixun Peng; Yihua Zhang

doi:10.1039/c1cc11633a

DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism

Chem Commun (Camb). 2011 Sep 7;47(33):9495-7. doi: 10.1039/c1cc11633a. Epub 2011 Jul 15.

Authors

Ye Ding¹, Zhangjian Huang, Jian Yin, Yisheng Lai, Shibo Zhang, Zhiguo Zhang, Lei Fang, Sixun Peng, Yihua Zhang

Affiliation

¹ Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China.

PMID: 21766102
DOI: 10.1039/c1cc11633a

Abstract

A novel and facile DDQ-mediated dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones is described. The formation of lactones proceeds by a radical ion mechanism, which has been established by DPPH˙-mediated chemical identification, ESR spectroscopy and an enol intermediate trapping.

MeSH terms

Benzoquinones / chemistry*
Biphenyl Compounds / chemistry
Free Radicals / chemistry
Ions / chemistry
Lactones / chemical synthesis
Lactones / chemistry*
Oleanolic Acid / analogs & derivatives
Oleanolic Acid / chemistry*
Picrates / chemistry

Substances

2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid
Benzoquinones
Biphenyl Compounds
Free Radicals
Ions
Lactones
Picrates
dichlorodicyanobenzoquinone
Oleanolic Acid
1,1-diphenyl-2-picrylhydrazyl