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Asymmetric Synthesis of 1,3‐Dithiolane Nucleoside Analogues
Author(s) -
Caputo Romualdo,
Guaragna Annalisa,
Palumbo Giovanni,
Pedatella Silvana
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390040
Subject(s) - dithiolane , chemistry , nucleoside , moiety , stereochemistry , enantiomer , sharpless epoxidation , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)