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Synthesis of gem-difluoromethylenated analogues of boronolide.

ABSTRACT: The straightforward synthesis of four gem-difluoromethylenated analogues 4-7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a-b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing building block 11 and the efficient construction of alpha,beta-unsaturated-delta-lactones 15a-b via BAIB/TEMPO-procedure.

SUBMITTER: Lin J

PROVIDER: S-EPMC2874314 | biostudies-other | 2010

REPOSITORIES: biostudies-other

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Synthesis of gem-difluoromethylenated analogues of boronolide.

Lin Jing J Qiu Xiao-Long XL Qing Feng-Ling FL

Beilstein journal of organic chemistry 20100420

The straightforward synthesis of four gem-difluoromethylenated analogues 4-7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a-b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing building block 11 and the efficient construction of alpha,beta-unsaturated-delta-lactones 15a-b via BAIB/TEMPO-procedure. ...[more]

PMID: 20502653

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