The chemical and microbiological synthesis of 14-hydroxy-gibberellins

descriptionPublicationkeyboard_double_arrow_right Article 01 Sep 1992 Spain English Publisher:Elsevier BVJournal:Tetrahedron, volume 48, pages 8,491-8,504 (issn: 0040-4020,

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Authors: Fraga, Braulio M.; García-Tellado, Fernando; González, Pedro; Hernández, Melchor G.; Hanson, James R.;

doi: 10.1016/s0040-4020(01)86597-2

handle: 10261/21871

The chemical and microbiological synthesis of 14-hydroxy-gibberellins

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Abstract

Gibberellic 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.

We thank Drs. A. San Martín and J. Rovirosa (University of Chile) for samples of ent-19-hydroxy-beyer-15-ene; Abbot Laboratories, Chicago, USA, for samples of gibberellic ecid and the CICYT, Madrid, for financial support.

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Spain

Related Organizations

University of Sussex
United Kingdom
Spanish National Research Council
Spain
University of La Laguna
Spain
Instituto de Productos Naturales y Agrobiología
Spain

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