Studies on Horner-Wadsworth-Emmons reaction in base sensitive ketones: Synthesis of (-)-mitsugashiwalactone and formal synthesis of (+)-iridomyrmecin, (-)-isoiridomyrmecin and (+)-teucriumlactone

Article abstract of DOI:10.1016/0040-4020(96)00023-3

The effect of different bases in promoting Horner-Wadsworth-Emmons (HWE) reaction on enolisable cyclopentanones is investigated. NaH is found to be suitable for the intermolecular reaction and DBU/LiCl is optimal for the intramolecular variation. The HWE approach is employed for the enantioselective synthesis of iridoid cyclopentapyranones of type-I (4, 16, 52) and type-II (5, 36).