65243-75-6Relevant articles and documents
Ring contraction through epoxide rearrangement: A formal synthesis of capsorubin
Constantino, Mauricio Gomes,Donate, Paulo Marcos,Frederico, Daniel,Carvalho, Tecia Vieira,Cardoso, Luiz Eduardo,Zukerman-Schpector, Julio
, p. 3327 - 3340 (2007/10/03)
An eight-step synthesis of the cyclopentane keto-alcohol 2, which has previously been converted in one step into the carotenoid pigment capsorubin (1), is described. The key step in our synthesis is a stereospecific epoxide rearrangement with ring contraction, thus producing the cyclopentane ring from an epoxide of a cyclohexene.
Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin
Bowden, Roy D.,Cooper, Robin D. G.,Harris, C. John,Moss, Gerard P.,Weedon, Basil C. L.,Jackman, Lloyd M.
, p. 1465 - 1474 (2007/10/02)
The two oxygen substitutents in the end groups of capsorubin were shown to be trans to one another by synthesis of optically inactive forms of the carotenoid, and of the isomers which have the corresponding cis-structure.The 3S,5R,3'S,5'R configuration thus established for the natural carotenoid was confirmed by synthesis of this stereoisomer from (+)-camphor.Cryptocapsin has the 3'S,5'R configuration, and the racemic form has been synthesised.Capsanthin has the 3R,3'S,5'R configuration.