2-(2-NITROETHYL)-1,3-DIOXOLANE AS REAGENT FOR 3-OXOPROPYL ANION SYNTHON: A NEW ROUTE TO JASMONOID AND PROSTAGLANDIN INTERMEDIATES

Article abstract of DOI:10.1016/S0040-4020(01)88811-6

2-(2-Nitroethyl)-1,3-dioxolane is a versatile reagent for 3-oxopropyl anion synthon.New methodology, based on nitroaldol condensation, oxidation and direct or indirect denitration sequence is developed for the conversion of 2-(2-nitroethyl)-1,3-dioxolane into (Z)-1,4-dioxodec-7-ene, (Z)-2-(2-pentenyl)-2-cyclopenten-1-one, methyl 9,12-dioxododecanoate and methyl 7-(5-oxocyclopentenyl)heptanoate, which are popular intermediates for syntheses of (Z)-jasmonoids and prostaglandins.