82266-70-4Relevant academic research and scientific papers
A NOVEL, VERSATILE SYNTHETIC APPROACH TO LINEARLY FUSED TRICYCLOPENTANOIDS via PHOTO-THERMAL OLEFIN METATHESIS
Mehta, Goverdhan,Srikrishna, A.,Reddy, A. Veera,Nair, Mangalam S.
, p. 4543 - 4559 (2007/10/02)
Fifteen examples of a new, speedy and general approach to linearly fused tricyclopentanoids bearing the tricyclo2,6>undecane (triquinane) frame of high contemporary interest is delineated.The key concept in our synthetic sequence to tri
A novel, versatile synthetic approach to linearly fused tricyclopentanoids via photo-thermal olefin metathesis
Mehta, Goverdhan,Srikrishna,Veera Reddy,Nair, Mangalam S.
, p. 4543 - 4559 (2014/12/10)
Fifteen examples of a new, speedy and general approach to linearly fused tricyclopentanoids bearing the tricyclo[6.3.0.02.6]undecane (triquinane) frame of high contemporary interest is delineated. The key concept in our synthetic sequence to triquinanes is the novel photo-thermal olefin metathesis of cheap, abundantly available Diels-Alder adducts of 1,3-cyclopentadienes and p-benzoquinones. Thus, photolysis of endo-tricyclo[6.2.1.02,7]undeca-4,9-dien-3,6-diones (9a-j, 13a,b)furnished pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8,11-diones (10a-j 14a, b), which on thermal fragmentation of the cyclobutane ring gave cis, syn, cis-tricyclo [6.3.0.02,6]undeca-4,9-dien-3,11-diones (11a-j, 15a,b) in just three steps and in exceptionally good yields. A few interesting transformations of the readily available parent bis-enone 11a which indicates its wider uses in syntheses, are described. Finally, a smooth thermal isomerisation of cis, syn, cis-bis-enones to cis, anti, cis-bis-enones is reported, which further enhances the scope and versatility of our synthetic theme.
