期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 20, 页码 8016-8020出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo8015192
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资金
- Natural Sciences and Engineering Research Council of Canada
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 center dot H2O, which results in removal of the tertbutyl group and spontaneous decarboxylative aromatization. The method was applied to the synthesis of the antimicrobial fungal metabolite culpin.
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