Directed metallations of 4-ethylidenetetronic acid and its derivatives as a synthetic entry to natural 4-oxy-2-furanones

Lithium diisopropylamide (LDA) removes the α-proton from the O-methyl tetronic acid (2$\text{b}$) leading to the vinylic carbanion (12), whereas treatment of the trimethylsilyl derivative (14) with LDA, followed by reaction with aldehydes gives products resulting from both γ? and ε-addition; the directed metallations provide access to a range of 4-oxy-2-furanone derivatives found amongst natural products.