An efficient method for the synthesis of substituted 4-acetoxynaphthalene- 2-carboxylate esters, ethyl 4-acetoxybenzofuran-6-carboxylate, and ethyl 4-acetoxybenzothiophene-6-carboxylate

Article abstract of DOI:10.1515/HC.2003.9.6.587

4-Acetoxynaphthalene-2-carboxylate esters and their corresponding benzofuran and benzothiophene esters are important synthetic intermediates for the preparation of analogs of CC-1065 and the duocarmycins. In this communication, an efficient method for the synthesis of the titled compounds using an Emmons-Horner reaction strategy is reported. As an alternative to the Stobbe condensation reaction, coupling of tert-butyl 3-ethoxycarbonyl-3- (phosphonodiethyl)propionate with a series of aromatic aldehydes, followed by acid promoted removal of the tert-butyl group and Friedel-Crafts reaction, produced the target compounds in good overall yields and of excellent quality.

Full text of DOI:10.1515/HC.2003.9.6.587

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Brought to you by | Purdue University Libraries
Authenticated | 10.248.254.158
Download Date | 8/29/14 2:08 AM

Brought to you by | Purdue University Libraries
Authenticated | 10.248.254.158
Download Date | 8/29/14 2:08 AM

Brought to you by | Purdue University Libraries
Authenticated | 10.248.254.158
Download Date | 8/29/14 2:08 AM

Brought to you by | Purdue University Libraries
Authenticated | 10.248.254.158
Download Date | 8/29/14 2:08 AM

Brought to you by | Purdue University Libraries
Authenticated | 10.248.254.158
Download Date | 8/29/14 2:08 AM