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Título: | Neighbouring group participation in the reaction of 7-oxo-ent-kaur-16-ene derivatives with diacetoxyiodobenzene. Synthesis of gibberellin analogues |
Autor: | Fraga, Braulio M. CSIC; Bressa, Carlo CSIC ORCID; González-Vallejo, Victoria CSIC; Suárez, Sergio; Guillermo, Ricardo CSIC | Fecha de publicación: | 28-dic-2011 | Editor: | Elsevier BV | Citación: | Tetrahedron Letters 52(52): 7138-7140 (2011) | Resumen: | The reaction of different 7-oxo-ent-kaur-16-ene derivatives with diacetoxyiodobenzene has been evaluated for the preparation of gibberellin analogues. Thus, the reaction of 7-oxo-ent-kaur-16-en-18-oic acid methyl ester (3) with this reagent afforded 4-epi-GA12 dimethyl ester (6). This reaction constitutes a good procedure for the preparation of this type of compounds. In some cases, alternative reactions that led to the introduction in the substrate of a conjugated 5,6-double bond or to the formation of a ketal at the 6-position were also produced. The formation of these compounds, or of gibberellin analogues, depends on the neighbouring group participation of the different C-18 and C-19 substituents at C-4. | Versión del editor: | http://dx.doi.org/10.1016/j.tetlet.2011.10.111 | URI: | http://hdl.handle.net/10261/205377 | DOI: | 10.1016/j.tetlet.2011.10.111 | Identificadores: | doi: 10.1016/j.tetlet.2011.10.111 issn: 0040-4039 |
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