Methyl 4-oxothiolane-3-carboxylate and methyl 2-methyl-4-oxothiolane-3-carboxylate anions as synthetic equivalents of α-acrylate and α-crotonate anions. Formal synthesis of integerrinecic acid.
- P. BARALDI
- GUARNERI MARIO
- POLLINI GIAN PIERO
- SIMONI DANIELE
- BARCO ACHILLE
- BENETTI SIMONETTA.
DOIAbstract
Base-promoted fragmentation of oxothiolanecarboxylates I [R = H, R1 = CH2Ph, CH2CO2Et, CH2C≡CH, CH2CH:CH2, CH2C6H4NO2-p, CH2C(OEt):CHCO2Et, (CH2)5Me, CH2R2 (R2 = phthaloyl); R = Me, R1 = CH2Ph, CH2CO2Et, CH2C≡CH, CH2CH:CH2, CH2C6H4NO2-p] with 5% NaOH at room temp. gave the corresponding RCH:CR1CO2Me in 41-90% yield. The technique was used in a formal synthesis of integerrinecic acid starting from I [R = Me, R1 = (CH2)2COMe]
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