ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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
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.
Chemical Papers 67 (1) 66–75 (2013)