Dioxolanones as synthetic intermediates. Part 3. Biomimetic synthesis of pulvinic acids

Robert Ramage, Gareth J. Griffiths, John N. A. Sweeney
1984 Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-organic Chemistry  
The reaction of the phosphorane (1 6) with methyl arylglyoxylates gives 5-(a-methoxycarbonyIarylidene) -2,2-pentamethylene-1,3-dioxolan-4-ones [ 5'(~-methoxycarbonylarylidene)cyclohexanespiro-2'-(1 ',3'-dioxolan) -4'-ones] which have been treated with the lithium enolates of t-butyl phenylacetic esters to provide a biomimetic synthesis of pulvinic acids. By this method pulvinic acid (2), vulpinic acid (1 ), and the unsymmetrically substituted compounds, leprapinic acid (3), and xerocomic acid
more » ... nd xerocomic acid (4) have been prepared; the last named was obtained via an intermediate (28) in which the phenolic groups were protected as benzyl ethers.
doi:10.1039/p19840001547 fatcat:ofupbb4kx5cvto5dbivj6vsg4q