Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 Jun 4;11(11):2285-8.
doi: 10.1021/ol900590t.

Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones

Affiliations

Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones

Branko Mitasev et al. Org Lett. .

Abstract

Manganese(III)-mediated oxidative transformations of dearomatized phloroglucinol (1,3,5-trihydroxybenzene) derivatives are reported. A number of cyclization modes have been observed, including polycyclization to afford bicyclo[2.2.2]octadiones via a formal oxidative radical [4 + 2] cycloaddition.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4

Similar articles

Cited by

References

    1. Snider BB, Patricia JJ, Kates SA. J. Org. Chem. 1988;53:2137.
    2. Kates SA, Dombroski MA, Snider BB. J. Org. Chem. 1990;55:2425.
    3. Snider BB, McCarthy BA. J. Org. Chem. 1993;58:6217.
    4. Snider BB. Chem. Rev. 1996;96:339. - PubMed
    5. Cole BM, Han L, Snider BB. J. Org. Chem. 1996;61:7832. - PubMed
    1. Melikyan GG. Synthesis. 1993:833.
    2. Mellor JM, Mohammed S. Tetrahedron. 1993;49:7557.
    3. Snider BB, Han L, Xie C. J. Org. Chem. 1997;62:6978.
    4. Chowdhury FA, Nishino H, Kurosawa K. Tetrahedron Lett. 1998;39:7931.
    5. Tsai A-I, Lin C-H, Chuang C-P. Heterocycles. 2005;65:2381.
    1. Williams GJ, Hunter NR. Can. J. Chem. 1976;54:3830.
    2. Dunlap NK, Sabol MR, Watt DS. Tetrahedron Lett. 1984;25:5839.
    3. Gross RS, Kawada K, Kim M, Watt DS. Synth. Commun. 1989;19:1127.
    4. Tanyeli C, Sezen B, Iyigun C, Elmali O. Tetrahedron Lett. 2001;42:6397.
    1. Bhowmik DR, Venkateswaran RV. Tetrahedron Lett. 1999;40:7439.
    1. Baran PS, DeMartino MP. Angew. Chem. Int. Ed. 2006;45:7083. - PubMed
    2. DeMartino MP, Chen K, Baran PS. J. Am. Chem. Soc. 2008;130:11546. - PubMed

Publication types

MeSH terms