General strategy for stereoselective synthesis of 1-substituted Exo,Endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Total synthesis of (±)-gmelinol

Manat PohmakotrAttapol PinsaTipwan MophuangPatoomratana TuchindaSamran PrabpaiPalangpon KongsaereeVichai ReutrakulMahidol University2018-08-202018-08-202006-01-06Journal of Organic Chemistry. Vol.71, No.1 (2006), 386-389002232632-s2.0-31144470193https://repository.li.mahidol.ac.th/handle/20.500.14594/23182A general strategy for stereoselective synthesis of 1-substituted exo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes including (±)-gmelinol from (2,3-trans)-(4,5-cis)-α-aroylparaconic esters, which are readily obtained from the reaction of vicinal dianions derived from α- aroylsuccinic esters with aromatic aldehydes, is described. The synthetic sequence involves α-methylation or α-hydroxylation, reduction, bislactonization, and reduction followed by furofuran formation. © 2006 American Chemical Society.Mahidol UniversityChemistryGeneral strategy for stereoselective synthesis of 1-substituted Exo,Endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Total synthesis of (±)-gmelinolArticleSCOPUS10.1021/jo0519110