75370-69-3Relevant academic research and scientific papers
Diastereoselective Synthesis of cis- or trans-2,3-Substituted Tetrahydrofurans and 3,4-Substituted 4-Butanolides
Frauenrath, Herbert,Philipps, Thomas
, p. 1951 - 1961 (2007/10/02)
Improved synthesis of 10 and the epimerisation 10 --> 11 yield cis- and trans-tetrahydro-3-furancarbaldehydes (10,11) with high diastereoselectivity. 10 as well as 11 are reduced by the Wolff-Kishner procedure to give 2-substituted 3-methyltetrahydrofurans 15 with trans configuration. 2-Substituted 3-methyltetrahydrofurans with cis configuration 14 are synthesized via 10 --> 12 --> 13 --> 14.The furans 14 and 15 possess structural features of naturally occurring 4-butanolides like quercus lactone a, quercus lactone b, or eldanolide which is the pheromone of the sugarcane borer Eldana saccharina (Wlk.). 14 and 15 are readily oxidized with CrO3/Ac2O to yield the lactones 16 and 17, whereas oxidation with Ru oxides proved to be less effective.The synthesis of rac-1 and rac-2 is described.
Reactions of Cyclic Acetale Carboxonium Ions, VI. The Stereoselectivity of the Acid-catalysed Rearrangement of 4,5-Dihydro-1,3-dioxepins to Tetrahydrofuran-3-carbaldehydes
Frauenrath, Herbert,Runsink, Jan,Scharf, Hans-Dieter
, p. 2728 - 2743 (2007/10/02)
The acid-catalysed rearrangement of 4,5-dihydro-1,3-dioxepins (1) leads under kinetically controlled conditions, contrary to other reports, stereoselectively to (Z)-tetrahydrofuran-3-carbaldehydes (2).At higher temperatures the thermodynamically more stab
Fragmentation of Cyclic Carboxonium Ions, III. 1,3-Dioxepan-4-ylium Ions, a Key for the Synthesis of Tetrahydrofuran-3-carbaldehydes
Scharf, Hans-Dieter,Frauenrath, Herbert
, p. 1472 - 1479 (2007/10/02)
The formation of 1,3-dioxepane-4-ylium ions (3) is achieved by protonation of 4,5-dihydro-1,3-dioxepines (2).These are prepared by ?-bond isomerization of 4,7-dihydro-1,3-dioxepines (1) under basic conditions.Thermal fragmentation of 3 and subsequent recy
