Published in
Elsevier, Tetrahedron Letters, 49(30), p. 6899-6902
DOI: 10.1016/s0040-4039(01)93383-0
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The first partial synthesis of 14-hydroxy-gibberellin esters. A titanium (IV)-amide catalysed rearrangement of epoxides
Journal article published in 1989 by
Braulio M. Fraga,
James R. Hanson,
Melchor G. Hernández,
Fernando G. Tellado 
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Abstract
Methyl gibberellate has been efficiently transformed into the 14β-hydroxygibberellin A7 methyl ester. The key step in the conversion was the rearrangement of the 3β-acetoxy-15β, 16β-epoxy-beyergibberellin A7 methyl ester to the target gibberellin ester by means of a titanium-amide pair, which is compatible with the highly reactive ring A of the gibberellin system.