Cyclotrimerization of 'Oxabenzonorbornadiene': Synthesis of syn- and anti-5,6,11,12,17,18-hexahydro-5,18:6,11 : 12,17-triepoxytrinaphthylene


De Lucchi O., Dastan A., Altundas A., Fabris F., Balci M.

HELVETICA CHIMICA ACTA, vol.87, no.9, pp.2364-2367, 2004 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 87 Issue: 9
  • Publication Date: 2004
  • Doi Number: 10.1002/hlca.200490213
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2364-2367

Abstract

An efficient synthetic route to the concave-shaped, potentially ionophoric syn- and anti-isomers of 5,6,11,12,17,18-hexahydro-5,18:6,11:12,17-triepoxytrinaphthylene (4) was elaborated. Starting from 'oxabenzonorbornadiene' (5), the stannylated precursor 9 was prepared in three steps, followed by cyclotrimerization ;catalyzed by copper(I) thiophene-2-carboxylate (CuTC), which afforded 4 in a synlanti ratio of 5:4.