Routes to drimanes from podocarpic acid

The synthesis and ozonolysis of the 6- and 7-substituted 12-hydroxypodocarpatrienes (26), (86), (90), and (98), as a possible route for the synthesis of drimanes from 12-hydroxypodocarpa-8,11,13-trien-19-oic acid (podocarpic acid) (9) has been investigated. Modification of the aromatic ring of (9) has given 11- and l4-hydroxypodocarpatrienes which were ozonised to give the congeners (31), (34), and (36) of the naturally occurring drimanes confertifolin (6), isodrimenin (7), and winterin (8). The oxidation of a 12,13-dihydroxypodocarpatriene (37) and its dimethyl ether (38) have also been investigated. Routes for the conversion of the enone (45) and oxime (230), derived from the ozonolysis products of methyl podocarpate (10), to drimanes have also been investigated.

Name thesis:degree_name

PhD

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Chemistry

Grantor dc:publisher

ResearchSpace@Auckland

Year dc:date.issued

1989

Author dc:creator

• Grimsdale, Andrew Clive

Advisor dc:contributor.advisor

• Professor Con Cambie

Statement dc:rights

• Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Licence dc:rights.uri

• https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm

Language dc:language.iso

en

Handle dc:identifier.uri

https://hdl.handle.net/2292/2072

OAI identifier oai:identifier

oai:researchspace.auckland.ac.nz:2292/2072