Synthesis of the Fungal Lipo-Chitooligosaccharide Myc-IV (C16:0, S), Symbiotic Signal of Arbuscular Mycorrhiza

摘要

A new synthesis of the fungal lipo-chitooligosaccharide Myc-IV (C16:0, S), which was recently reported to be a major symbiotic signalling molecule in arbuscular mycorrhiza, is described. Key steps include the oxidative cleavage of a 4,6-Obenzylidene acetal to prepare a disaccharidic glycosyl acceptor, and stereoselective glycosylations with 2-methyl-5-tert-butylphenyl thioglycosyl donors.