Synthesis of methyl secolonitoside

Abstract

The monoterpene diglycoside macrolide, lonitoside 1, is assumed to be biosynthesized via the intermediate acid secolonitoside 3 which has also been isolated from Lonicera nitida E. H. Wilson. We have synthesized the methyl ester of acid 3 from D-glucose, L-arabinose and (-)-citronellol [via methyl (E,S)-8-hydroxy-2,6-dimethyloct-2-enoate], both as a formal proof of structure and as an approach to a total synthesis of the macrolide 1.