D. Belluš, Pierre Martin, H. Sauter
Jul 9, 1980
Citations
0
Influential Citations
15
Citations
Journal
Helvetica Chimica Acta
Abstract
Syntheses of 3-Hydroxy-4-methyl-3-cyclobutene-1,2-dione (Methylmoniliformin) New routes to 3-hydroxy-4-methyl-3-cyclobutene-1,2-dione (9), the lowest homologue of the mycotoxine moniliformin are described. A common feature of all pathways is the synthesis of methylcyclobutanes having the oxidation level 6. Precursors, which are easily transformed to 9 by acid catalyzed hydrolysis, include [2+2]-cycloadducts of in situ generated methyl ketene to tetraethoxyethylene and [2+2]-photocycloadducts of dichlorovinylenecarbonate with 1,1-dichloro-1-propene. The acid hydrolysis of [2+2]-cycloadducts of chlorotrifluoroethylene to N, N-diethyl-1-propynylamine yields the diethylamide of 9 (=22) in 50% overall yield. In addition, a convenient one-pot-two-steps synthesis of a new electronrich ethylene, 1,1,2-triethoxy-2-trimethylsilyloxy-ethylene (11), is described.