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

[摘要]：A method is described for converting tert-Bu benzoates or tert-Bu 1-naphthoates into derivs. 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) addn. of an organometallic species to a cross-conjugated cyclohexadienone obtained by Birch alkylation of a tert-Bu benzoate or a tert-Bu 1-naphthoate, followed by allylic oxidn., and (ii) treatment with BiCl3譎2O, which results in removal of the tert-Bu group and spontaneous decarboxylative aromatization. The method was applied to the synthesis of the antimicrobial fungal metabolite culpin.

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