Expansion of ring B in the gibberellins: Entry to the Rabdosia family of kaurenoids

Authors
Benjamin, LJ Adamson, G Mander, LN
Citation
Lj. Benjamin et al., Expansion of ring B in the gibberellins: Entry to the Rabdosia family of kaurenoids, HETEROCYCLE, 50(1), 1999, pp. 365-375
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
1
Year of publication
1999
Pages
365 - 375
Database
ISI
SICI code
0385-5414(19990101)50:1<365:EORBIT>2.0.ZU;2-E
Abstract
The Lewis acid or base-catalysed rearrangement of an a-hydroxy aldehyde der ived from the gibberellin GA(15) results in ring-expansion of the 5-membere d B-ring of the gibberellin molecule and transformation into an ent-kaurene derivative. Further manipulation affords 19,7-acetals and access to the hi ghly functionalised kaurenoid secondary metabolites that have been isolated from the genus Rabdosia.