Asymmetric Synthesis of 1,3‐Dithiolane Nucleoside Analogues | Zendy

Caputo Romualdo | Zendy; Guaragna Annalisa | Zendy; Palumbo Giovanni | Zendy; Pedatella Silvana | Zendy

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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)

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