- Synthetic scheme for the preparation of 13C-labeled 3,4-didehydro-retinal, 3-hydroxyretinal, and 4-hydroxyretinal up to uniform 13C-enrichment
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A modular synthetic scheme has been developed for the synthesis of 13C-labeled naturally occurring visual pigment chromophores; 3,4-didehydroretinal, 3-hydroxyretinal, and 4-hydroxyretinal. These compounds can now be made with > 99% 13C enrichment at any position or combination of positions. We used the common C10+C5+C5 scheme for the synthesis of retinals, and by making variations in the C10 part we can now prepare the desired retinal derivatives with selective or uniform 13C enrichment. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Van Wijk, Arjan A. C.,Van de Weerd, Michiel B.,Lugtenburg, Johan
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- γ-Pyronene, a synthon derived from saffron and intermediary precursor of synthesis of forskolin and strigol
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γ-Pyronene, a terpenic synthon available from myrcene, is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes, retinoids and biological derivatives such as forskolin or strigol.
- Boulin,Arreguy-San Miguel,Delmond
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p. 2753 - 2762
(2007/10/03)
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- Syntheses of high specific activity 2,3- and 3,4-[3H]2-9-cis-retinoic acid
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9-cis-Retinoic acid (9-cis-RA) is an endogenous hormone which binds and activates the retinoic acid receptors (RARs) and the retinoic X receptors (RXRs). In order to investigate the function of 9-cis-RA in vitro and in vivo high specific activity labeled 9-cis-RA was prepared. Two tritium labels were efficiently introduced at the 2,3- or 3,4-positions, respectively, in the cyclohexene ring moiety resulting in labeled 9-cis-RA with specific activity of 58-60 Ci/mmol. The critical ring-labeling step relies on a highly regioselective tritiation of either a terminal or an isolated double bond in the presence of the conjugated retinoate side chain. Moreover, the labeling is performed at the penultimate synthetic step resulting in optimization of radiochemical yields and ease of synthesis. This is the first reported synthesis of ring-labeled [3H]2-9-cis-Ra, and the methodology described herein is applicable to the synthesis of other retinoic acid isomers.
- Bennani,Boehm
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p. 1195 - 1200
(2007/10/02)
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- The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues
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Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues.The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2).In addition, thujone-drived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues.In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed.In summary, these studies afford an attractive versatile route to these important perfumery materials.
- Kutney, James P.,Gunning, Philip J.,Clewley, Robin G.,Somerville, John,Rettig, Steven J.
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p. 2094 - 2114
(2007/10/02)
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- Reaction of Ester Enolates with Nucleophiles. Stereocontrolled Formation of Ketone and Aldehyde Enolates
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Lithium enolates of carboxylic and thiocarboxylic esters react with nucleophiles to afford ketone and aldehyde enolates and subsequently their enol silyl ethers diastereoselectively.This reaction is applied to the synthesis of γ-damascone, α-damascone, β-safranal, and artemisia ketone.
- Fehr, Charles,Galindo, Jose
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p. 1828 - 1830
(2007/10/02)
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