83538-15-2Relevant academic research and scientific papers
Stereospecific Cyclization of 2-(3-Hexenyl)-1,3-dimethyl-2-cyclohexen-1-ol with Z- and E-Configuration
Brunke, Ernst-Joachim,Hammerschmidt, Franz-Josef,Struwe, Hartmut
, p. 3128 - 3140 (2007/10/02)
Cyclization of 4a (Z) with formic acid leads selectively to the products with trans-configurated side chain: 5a (byproduct), 6a, and 7a.Starting from 4b (E), the products with cis-configurated side chain are exclusively formed: 5b (byproduct), 6b, and 7b.The constitution of the cyclization products was demonstrated by degradation to the diketones 10, 11.The elucidation of the relative configuration at C-7 was achieved by oxidation of 5a and 6a to 12a (trans), 5b and 6b to 12b (cis), 7a to 13a (trans), and 7b to 13b (cis).By alkaline equilibration of 12a/12b and13a/13b the correlation between the stereochemical series was delineated.Reduction of the ketones gave 5a (from 12a), 5b (from 12b), 14a (from 13a), and 14b (from 13b).By this, all the diastereomeric racemates, which are possible in these series, were prepared and the relative configurations, given above, could be demonstrated.
