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Issue 37, 2014
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Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

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Abstract

DFT calculations probing potential (4 + 2) and (4 + 3) cycloaddition pathways leading to the polycyclic ring systems found in the coral secondary metabolites plumarellide, mandapamate and rameswaralide are described. Formation of plumarellide and mandapamate via stepwise intramolecular cycloaddition of a furanoxonium ion onto a 1,3-diene is shown to be viable. The calculations also predict the outcome of related cyclisations involving model systems.

Graphical abstract: Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

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Publication details

The article was received on 07 Apr 2014, accepted on 31 Jul 2014 and first published on 01 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB00734D
Citation: Org. Biomol. Chem., 2014,12, 7270-7278
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    Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

    B. Lygo, M. J. Palframan and G. Pattenden, Org. Biomol. Chem., 2014, 12, 7270
    DOI: 10.1039/C4OB00734D

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