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

Total synthesis of N,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener

Miroslava Martinková, Kvetoslava Pomikalová, and Jozef Gonda

Department of Organic Chemistry, Institute of Chemical Sciences, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia

E-mail: miroslava.martinkova@upjs.sk

Abstract: Total synthesis of the natural d-ribo-phytosphingosine I and its 2-epimer III in the protected form was achieved through a common strategy. The aza-Claisen rearrangement of allylic thiocyanate (Z)-V incorporated the new stereogenic centre with nitrogen and the subsequent Wittig olefination constructed a non-polar side chain. Hydrogenation, followed by removal of protecting groups, completed the syntheses of I and III.

Keywords: phytosphingosine – aza-Claisen rearrangement – microwave irradiation – isothiocyanates

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-012-0245-0

Chemical Papers 67 (1) 84–91 (2013)