99488-07-0Relevant 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.
