β- and α-LITHIATION OF METHYL β-METHOXYACRYLATE: EFFICIENT SYNTHESIS OF α,γ-SUBSTITUTED METHYL TETRONATES - STRUCTURE OF ASPERTETRONINS AND GREGATINS

Article abstract of DOI:10.1016/S0040-4039(00)86743-X

Methyl β-methoxyacrylate (1) can be lithiated succesively in β- and α-positions.Reaction with two electrophiles (at first a carbonyl compound) leads to α,γ-substituted methyl tetronates in a two step synthesis.Application of this method to the synthesis of methyl tetronate whose structure was assigned as that of gregatin B indicates that the gregatins and aspertetronins have the isomeric structures 17.