- Preparation of (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone and derivatives and stereoisomers of this compound
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A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia which is required for preparing the red dye capsorubin
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- Ring contraction through epoxide rearrangement: A formal synthesis of capsorubin
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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.
- Constantino, Mauricio Gomes,Donate, Paulo Marcos,Frederico, Daniel,Carvalho, Tecia Vieira,Cardoso, Luiz Eduardo,Zukerman-Schpector, Julio
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p. 3327 - 3340
(2007/10/03)
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- Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin
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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.
- Bowden, Roy D.,Cooper, Robin D. G.,Harris, C. John,Moss, Gerard P.,Weedon, Basil C. L.,Jackman, Lloyd M.
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p. 1465 - 1474
(2007/10/02)
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