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The chemical and microbiological synthesis of 14-hydroxy-gibberellins

AuthorsFraga, Braulio M. ; García-Tellado, Fernando ; González, Pedro; Hernández, Melchor G.; Hanson, James R.
Issue Date1992
CitationTetrahedron 48(39): pp. 8491-8504 (1992)
AbstractGibberellic acid has been transformed into 14B-hydroxy-gibberellin A7 methyl ester via the rearrangement of an epoxy-beyergibberellin intermediate using a titanium-amide complex. The diterpene ent-beyer-15-en-19-ol has been transformed by chemical methods into ent-14a,19-dihydroxy-kaur-16-ene. The biotransformation of this compound with the fungus Gibberella fujokuroi gave 14B-hydroxy-gibberellin A7, ent 7a,14a,19-trihydroxy-kaur-16-ene and ent-6a,7a,14a-trihydroxy-kaur-16-en-oic acid. A minor gibberellin 14B-hydroxy-GA14 was identified by GC-MS.
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