@article { ISI:000333477500018,
	title = {Base-stimulated 1,2-, 1,4-, and 1,6-eliminations in suitably substituted alkylidenesuccinates leading to natural and unnatural conjugated alkenyl(methyl)maleic anhydrides},
	journal = {Journal of Organic Chemistry},
	volume = {79},
	number = {6},
	year = {2014},
	month = {MAR},
	pages = {2538-2546},
	publisher = {AMER CHEMICAL SOC},
	type = {Article},
	address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA},
	abstract = {<p>With dimethyl maleate as the starting material, facile stereoselective syntheses of natural and unnatural conjugated alkenyl(methyl)maleic anhydrides have been described. The key reactions were base-endorsed novel 1,2-, 1,4-, and 1,6-eliminations in the corresponding alkylidenesuccinate derivatives. The 1,2-eliminations in cyclic carbonate and sulfite by regioselective abstraction of methine protons with the respective release of CO2 and SO2 provided a conjugated ketone product. The characteristic 1,4- and 1,6-elimination reactions with respective release of acetone and mesylate furnished the corresponding unsaturated alcohols. The obtained allylic alcohols were transformed into conjugated alkenyl(methyl)maleic anhydrides via oxidation followed by a Horner-Wadsworth-Emmons reaction pathway in very good yields. The mechanistic aspects involved in these significant elimination reactions have also been described in brief.</p>},
	issn = {0022-3263},
	doi = {10.1021/jo402857r},
	author = {Deore, Prashant S. and N. P. Argade}
}
