Diastereoselective and convergent synthesis of both 11′-epimers of (-)-(2R,3R,6S)-carnavaline

Article abstract of DOI:10.1016/S0040-4020(97)00428-6

Enantio- and diastereoselective syntheses of both 11′-epimers of (-)-carnavaline 1 have been achieved. Since the configuration of the remote chiral centre in the C-12 side chain of naturally occurring (-)-carnavaline had been unknown and spectroscopic data were not conclusive, an assignment of the 11′S-epimer to the natural product by comparison of the melting points is discussed and complete spectroscopic data are given.