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

Stereoselective total synthesis of protected sulfamisterin and its analogues

Jana Špaková Raschmanová, Miroslava Martinková, Jozef Gonda, and Alena Uhríková

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: The stereoselective synthesis of sulfamisterin I and its unnatural analogues II and V in their protected form was achieved through a common strategy. The Wittig reaction of aldehydes VIII and IX with the C₁₄ hydrophobic side-chain X served as the key C-C connecting transformation. Subsequent functional group inter-conversions in the coupling products XI and XX completed the total synthesis.

Keywords: sulfamisterin – total synthesis – stereoselective – α-substituted α-amino acid – Wittig reaction – serine palmitoyltransferase

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0392-y

Chemical Papers 67 (10) 1317–1329 (2013)