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.

Autor: Lygo B; School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK., Palframan MJ, Pattenden G
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2014 Oct 07; Vol. 12 (37), pp. 7270-8.
DOI: 10.1039/c4ob00734d
Abstrakt: 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.
Databáze: MEDLINE