159928-92-4Relevant academic research and scientific papers
Studies of a novel biomimetic radical spirocyclisation
Topiwala, Upendra P.,Luszniak, Mark C.,Whiting, Donald A.
, p. 1185 - 1191 (2007/10/03)
The mechanism of the radical spirocyclisation 7→9 has been investigated. It has been shown by isotopic labelling that the biaryl ether oxygen does not emerge as the carbonyl group oxygen in the product, nor does the latter arise by hydrolysis of an intermediate e.g. 33 by added water. The mechanism of Scheme 1 path a is proposed, involving oxygen transfer from an aromatic nitro group to carbon in a cyclohexadienyl radical. Radical decarboxylation of the biarylamine derivative 29 does not lead to spirodienone 9 but diverts instead to the azathiaacetal 30.
New carbon radical chemistry as a model for the biogenesis of the interiorin/kadsulignan type of dibenzocyclooctadiene lignan
Green, Stuart P.,Whiting, Donald A.
, p. 193 - 201 (2007/10/03)
Novel intramolecular radical spirocyclisation reactions in aromatic nuclei, 48→49, 40→22 and 34→32, are presented, which mimic a key step in the proposed biosynthesis of the interiorins 2a-d, the kadsulignans 3a,b and relatives.
Biomimetic Spirocyclisation using Novel Intramolecular Radical Oxygenation; a Model for the Biosynthesis of the Interiorin Lignans
Green, Stuart P.,Whiting, Donald A.
, p. 2441 - 2442 (2007/10/02)
Novel intramolecular radical spirocyclisation reactions in aromatic nuclei, 22 -> 23 and 30 -> 31, are presented, which mimic a key step in the proposed biosynthesis of the interiorins 1-4 and kadsulignans 5, 6.
