99488-04-7

Upstream product

• 175154-68-4 Tetrahydro-2-phenylfuran-3-carbaldehyd 
• 100-52-7 benzaldehyde 
• 35174-10-8 2-phenyl-4,5-dihydro-[1,3]dioxepine 
• 56318-28-6 (bis(allyloxy)methyl)benzene 
• 2568-24-3 2-phenyl-4,7-dihydro-1,3-dioxepine 

Downstream Products

• 99488-10-5 cis-3-methyl-2-phenyltetrahydrofuran 
• 99488-10-5 (2α,3β)-(+/-)-Tetrahydro-3-methyl-2-phenylfuran 
• 99488-07-0 (2α,3α)-(+/-)-Tetrahydro-2-phenyl-3-(tosyloxymethyl)furan 

Relevant academic research and scientific papers

Lewis Acid-Catalyzed Vinyl Acetal Rearrangement of 4,5-Dihydro-1,3-dioxepines: Stereoselective Synthesis of cis- And trans-2,3-Disubstituted Tetrahydrofurans

Lewis acid-catalyzed rearrangements of 4,5-dihydro-1,3-dioxepines have been investigated. Rearrangement of vinyl acetals under a variety of conditions resulted in cis- and trans-2,3-disubstituted tetrahydrofuran derivatives in a highly stereoselective man

Diastereoselective Synthesis of cis- or trans-2,3-Substituted Tetrahydrofurans and 3,4-Substituted 4-Butanolides

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.