A detailed study is described of the reaction of methyl gibberellate (2), methylisogibberellate (4) and their corresponding tetrahydropyranyl ethers (3) and (5) with three cuprates, (LiCuMe2)2, Li2Cu3Me5, and (LiCu2Me3)2. The structures of the products, produced by displacement of the allylic lactone system by SN2 or SN2′syn and anti mechanisms, were deduced by extensive n.m.r. studies.
M. H. Beale, J. Chem. Soc., Perkin Trans. 1, 1985, 1151 DOI: 10.1039/P19850001151
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