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Synthesis of pseudouridines modified at the C-5′ position

✍ Scribed by T. Sato; M. Watanabe; R. Noyori

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
218 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

We have recently developed an efficient route to members of C-nucleoside antibiotics starting from acetone and furan. 1 Use of the oxabicyclooctenone I as the key intermediate permits the perfect stereochemical control throughout the overall transformation that consists of elaboration of the ribofuranosyl skeleton and introduction of the nitrogen bases into the C-l' position. Because of the versatility of the reductive 3 + 4 cyclocoupling reaction between polybromo ketones and furans, 2 this method finds a wide synthetic flexibility. Here we describe the first, ready structural modification of pseudouridine (II) at the C-5' position. HO OH II The bicyclic ketone IIIa, prepared from 1, 1,3-tribromo-3-methylbutan-2-one and furan, 3 was converted with complete stereoselectivity to the cz glycol acetonide IVa4 by the standard procedure (30% H202 -cat. 0s04/acetone-ether-tert-butyl alcohol, 25 "C, 12 h, and then E-TsOH--CuS04/acetone, 25 "C, 12 h, 59% yield). Subsequent Baeyer-Villiger oxidation with CF ?? C03H (3 equiv, CH2C12-phosphate buffer, 25 "C, 6 h) led regiospecifically to the lactone Va in 81% yield, which was reacted with bis(dimethylamino)-tert-butoxymethane6 (6.5 equiv, DMF, 50 "C, 3 h) to afford Via' in 96% yield. Condensation of Via with urea forming the uracil derivative VIIa8 was accomplished with 2.4 M ethanolic C2H50Na in 48% yield. This product was homogeneous on thin-layer chromatography with several solvent systems. The fi stereochemistry at the anomeric 1' position was confirmed by the NMR spectrum. 9 Finally, acid

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