Synthesis of tritium labelled 3(R)-HETE and 3(R),18(R/S)-DiHETE through a common synthetic route
β Scribed by Natalya V. Groza; Igor V. Ivanov; Stepan G. Romanov; Valery P. Shevchenko; Nikolai F. Myasoedov; Santosh Nigam; Galina I. Myagkova
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- French
- Weight
- 101 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0022-2135
- DOI
- 10.1002/jlcr.791
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β¦ Synopsis
Abstract
An efficient procedure for the synthesis of 3βhydroxyoxylipins labelled with tritium on all double bond positions is reported. The synthetic scheme involves a joint route for the formation of tetraacetylenic precursors followed by stereoselective reduction of the triple bonds either with hydrogen or tritium. The final tritiated products were obtained with specific activities ranging from 1.65 to 1.80 Ci/mmol. Copyright Β© 2003 John Wiley & Sons, Ltd.
π SIMILAR VOLUMES
S)-3-Aminoquinuclidine-3H 1 Oc-S having a specific activity of 66 Ci/mrnol was prepared in eight steps from lsonicotinic acid (2). Reduction of 2 with carrier free tritium gas over PtO2 In DMF gave isonipecotic acid-3H &. Conversion to a-bromo ketone followed by cyclization afforded 3-quinuclidone-
R) and (S)-3-aminoquinuclidines-3H with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3s) Chiraphos in methanol gave yacemk amide &. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyana
Short Synthetic Route to Retinoids Through Dialkylation of 3-Methyl-3-sulfolene. -Sequential alkylation of 3-methyl-3-sulfolene (I) with bromomethyl ether (II) followed by aldehyde (IV) provides a short and efficient route to retinol methyl ether (VII). An analogous sequence allows the preparation