Conversion of Gibberellic Acid into the B-Ring seco-Kaurenoid, Longirabdolactone

@inproceedings{Adamson2003ConversionOG,
  title={Conversion of Gibberellic Acid into the B-Ring seco-Kaurenoid, Longirabdolactone},
  author={George A. Adamson and Lewis N. Mander},
  year={2003}
}
The base-catalyzed rearrangement of an α-hydroxy aldehyde derived from the gibberellin GA15 results in ring-expansion of the five-membered B-ring of the gibberellin molecule and transformation into an ent-kaurene derivative. Further manipulation affords 19,7-acetals and access to the highly functionalized B-ring seco-kaurenoid bioactive secondary metabolites that have been isolated from the genus Rabdosia. The methodology is illustrated by the synthesis of longirabdolactone from gibberellic… CONTINUE READING

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