Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety
摘要
A stereoselective synthesis of new (6Z,10Z)-16-hydroxyhexadeca-6,10-dienoic and (7Z,11Z)-18-hydroxyoctadeca-7,11-dienoic acid that involved the Ti-catalyzed homocyclomagnesiation of the functionally substituted 1,2-dienes was developed. Subsequent intramolecular cyclization of the synthesized ω-hydroxyalkadienoic acids in the presence of catalytic amounts (2.5–10 mol.%) of hafnium(iv) triflate gave unsaturated macrocyclic lactones and diolides with pharmacophoric 1Z,5Z-diene moieties.