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Synthesis and Diels-Alder Reactivity of Substituted [4]Dendralenes

Saglam, Mehmet F; Alborzi, Ali R; Payne, Alan D; Willis, Anthony C; Paddon-Row, Michael N; Sherburn, Michael


The first synthesis of all five possible monomethylated [4]dendralenes has been achieved via two distinct synthetic strategies. The Diels-Alder chemistry of these new dendralenes (as multidienes) with an electron poor dienophile, N-methylmaleimide (NMM), has been studied. Thus, simply upon mixing the dendralene and an excess of dienophile at ambient temperature in a common solvent, sequences of cycloadditions result in the rapid generation of complex multicyclic products. Distinct product...[Show more]

CollectionsANU Research Publications
Date published: 2016-02-19
Type: Journal article
Source: The Journal of organic chemistry
DOI: 10.1021/acs.joc.5b02583
Access Rights: Open Access


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