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The first partial synthesis of 14-hydroxy-gibberellin esters. A titanium (IV)-amide catalysed rearrangement of epoxides

AuthorsFraga, Braulio M. ; Hanson, James R.; Hernández, Melchor G.; García-Tellado, Fernando
Issue Date1989
CitationTetrahedron Letters 30(49): pp. 6899-6902 (1989)
AbstractMethyl gibberellate has been efficiently transformed into the 14B-hydroxygibberellin A7 methyl ester. The key step in the conversion was the rearrangement of the 3B-acetoxy-15B, 16B-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.
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