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- Title
Synthesen von Moniliformin, einem Mycotoxin mit Cyclobutendion-Struktur.
- Authors
Belluš, Daniel; Fischer, Hanspeter; Greuter, Hans; Martin, Pierre
- Abstract
Syntheses of Moniliformin, a Mycotoxine with a Cyclobutenedione Structure Six different routes to 3-hydroxy-3-cyclobutene-1, 2-dione ( 4), the free acid of the mycotoxine Moniliformin (=alkali salt of 4) are described. A common feature of all pathways is the synthesis of cyclobutanes having the oxidation level 6. Moniliformin precursors which are easily transformed to 4 by acid catalysed hydrolysis include [2+2]-cycloadducts of ketene with tetraalkoxy-olefins, 3,4,4-trialkoxycyclobutenes, derivatives of polyfluorinated cyclobutenes, the brominated [2+2]-cycloadduct of ethyl vinyl ether and dichloroketene, tetrabromocyclobutanone, [2+2]-photocycloadducts of dichlorovinylenecarbonate with dichloroethylenes, and the dimer of chloroketene. The most convenient synthesis via the [2+2]-cycloadduct of tetraethoxyethylene and ketene ( 14b) is reported in detail and produces 4 in four simple steps in 57% overall yield. In addition, two new syntheses of squaric acid ( 56) are described.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 5, p1784
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610526