We report the ready asymmetric synthesis of nucleoside analogues containing a 1,3-dithiolane ring that mimics the sugar moiety of natural nucleosides. The synthesis is accomplished in three main steps from benzoyloxyethanal 1,3-dithiolane, the key step being its conversion into a chiral monosulfoxide by a modified Sharpless sulfo-oxygenation reaction. The nucleoside analogues were obtained in good overall yields and with excellent enantiomeric excesses.
Asymmetric synthesis of 1,3-dithiolane nucleoside analogues / Caputo, Romualdo; Guaragna, Annalisa; Palumbo, Giovanni; Pedatella, Silvana. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2(2003), pp. 346-350. [10.1002/ejoc.200390040]
Asymmetric synthesis of 1,3-dithiolane nucleoside analogues
CAPUTO, ROMUALDO;GUARAGNA, ANNALISA;PALUMBO, GIOVANNI;PEDATELLA, SILVANA
2003
Abstract
We report the ready asymmetric synthesis of nucleoside analogues containing a 1,3-dithiolane ring that mimics the sugar moiety of natural nucleosides. The synthesis is accomplished in three main steps from benzoyloxyethanal 1,3-dithiolane, the key step being its conversion into a chiral monosulfoxide by a modified Sharpless sulfo-oxygenation reaction. The nucleoside analogues were obtained in good overall yields and with excellent enantiomeric excesses.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
