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

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

Oľga Caletková, Diana Ďurišová, Naďa Prónayová, and Tibor Gracza

Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia

E-mail: tibor.gracza@stuba.sk

Abstract: Aminohydroxylation of prochiral divinylcarbinol and subsequent Pd(II)-catalysed oxy-/amidocarbonylation of aminopentenediols is reported. The method was applied to the preparation of useful building blocks for syntheses of cytotoxic jaspines and glycosidase inhibitor DLX-homologues. The key intermediates, tetrahydrofuranolactones (l-arabino-II) and pyrrolidinolactones (l-arabino-IX and l-xylo-IX), were prepared in a short 2-step sequence from divinylcarbinol.

Keywords: Sharpless aminohydroxylation – Pd(II)-catalysed oxy-/amidocarbonylation – jaspine B – pachastrissamine – DLX-homologues

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-012-0224-5

Chemical Papers 67 (1) 66–75 (2013)