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Utilisation of Diterpenoids for Synthesis

by Mitchell, Lorna Helen

Abstract (Summary)
The natural product triptoquinone F (27) was synthesised from podocarpic acid (1) through an acid-promoted Fries rearrangement of a benzannulated lactone (99); this method was introduced as a direct and high yielding route for C 11 functionalisation. The structure of the Fries rearranged product 117 was confirmed through synthesis by a known stepwise route from lactone 99. The scope of acid-promoted Fries rearrangement of benzannulated diterpenoid B ring lactones and some smaller bicyclic lactones was then examined. This reaction was found to be applicable to e-aryl lactones possessing a sufficiently activated aromatic ring, but was unsuccesslul for 6-aryl lactones. A methano-bridged benzoxocin compound 169 and two acylated derivatives of this were unexpectedly isolated from attempted Fries reanangement of 12,19-dimethoxy lactone 158.
Bibliographical Information:

Advisor:

School:The University of Auckland / Te Whare Wananga o Tamaki Makaurau

School Location:New Zealand

Source Type:Master's Thesis

Keywords:

ISBN:

Date of Publication:01/01/1998

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