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Título

Biotransformation of two ent-15B-hydroxy-kaur-16-ene derivatives by Gibbewrella fujikuroi

AutorFraga, Braulio M. ; Hernández, Melchor G.; González, Pedro
Palabras claveGibberella fujikuroi
Diterpenes
ent-15B-hydroxy-kaur-16-ene
Candidiol
Microbiological transformations
Fecha de publicación1992
EditorElsevier
CitaciónPhytochemistry 31(11): pp. 3845-3849 (1992)
ResumenIncubation of the fungus Gibberella fujikuroi with ent-15B-hydroxy-kaur-16-ene gave ent-11a, 15B-dihydroxy-kaur-16-ene, ent-7B,1]a,15B-trihydroxy-kaur-16-ene, ent-11a,13,15B-trihydroxy-kaur-16-ene, ent-11a,15B,19-trihydroxy-kaur-16-ene, and ent-11a,14a,15B-trihydroxy-kaur-16-ene, and a mixture of products, which was resolved by acetylation to give ent-11a,14a,15B-triacetoxy-kaur-16-ene and ent-7B,15B,17-triacetoxy-11a,16a-epoxy-kaur-16-ene. The addition of candidiol (ent-15B,18-dihydroxy-kaur-16-3n3) gave ent-11a,15B,18-trihydroxy-kaur-16-ene, and a mixture of substances, which was resolved by acetulation to give ent-11B,15B,18-triacetoxy-kaur-16-ene, ent-7B,11a,15B,18-tetraacetoxy-kaur-16-ene and ent-15B,17,18-triacetoxy-11a,16a-epoxykaurane. These results confirm that the presence in ent-kaur-16-ene derivatives of a 15a-hydroxyl group inhibits oxidation at C-19 to the acid level. The biotransformation of these compounds may be useful for the synthesis of natural 11B-hydroxy-ent-kaurene analogues.
URIhttp://hdl.handle.net/10261/21924
ISSN0031-9422
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