ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of sulfone analog of oseltamivir precursor

Viera Poláčková, Robert Šándrik, and Radovan Šebesta

Comenius University in Bratislava, Bratislava, Slovakia

E-mail: radovan.sebesta@uniba.sk

Abstract: We describe here the synthesis of a sulfone analog of an oseltamivir precursor. The synthesis comprises cyclization of two advanced building blocks via one-pot Michael addition and Horner–Wadsworth–Emmons reaction. The first building block was synthesized by an organocatalytic Michael addition of pentyloxyacetaldehyde to a nitroalkene. The second, alkenylsulfone, building block was prepared by oxidation followed by a Mannich type reaction. The cyclization was accomplished under microwave irradiation.

Keywords: Organocatalysis ; Oseltamivir analog ; Michael addition, cyclization 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0274-9

Chemical Papers 72 (1) 221–227 (2018)