Tetrahedron Letters

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

NG Clemo, G Pattenden

Index: Clemo, Nicholas G.; Pattenden, Gerald Tetrahedron Letters, 1982 , vol. 23, # 5 p. 581 - 584

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Citation Number: 25

Abstract

Summary: Lithium diisopropylamide (LDA) removes the a-proton from the O-methyl tetronic acid (2b) 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 y- and E-addition; the directed metallations provide access to a range of 4-oxy-2-furanone derivatives found amongst natural products. ... A wide variety of compounds containing the 4-oxy-2- ...