American Chemical Society
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A Route to 1,4-Disubstituted Aromatics and Its Application to the Synthesis of the Antibiotic Culpin

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journal contribution
posted on 2008-10-17, 00:00 authored by Rajesh Sunasee, Derrick L. J. Clive
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·H2O, 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.