1071817-53-2Relevant academic research and scientific papers
A route to 1,4-disubstituted aromatics and its application to the synthesis of the antibiotic culpin
Sunasee, Rajesh,Clive, Derrick L. J.
experimental part, p. 8016 - 8020 (2009/04/11)
(Chemical Equation Presented) A method is described for converting tert-butyl benzoates or tert-butyl 1-naphthoates into derivatives having an alkyl or substituted alkyl group in a 1,4-relationship to an alkyl, aryl, alkenyl, or alkynyl group. Key steps in the sequence are (i) addition of an organometallic species to a cross-conjugated cyclohexadienone obtained by Birch alkylation of a tert-butyl benzoate or a tert-butyl 1-naphthoate, followed by allylic oxidation, and (ii) treatment with BiCl3·H 2O, which results in removal of the tert-butyl group and spontaneous decarboxylative aromatization. The method was applied to the synthesis of the antimicrobial fungal metabolite culpin.
