UBC Theses and Dissertations

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UBC Theses and Dissertations

Function-oriented synthesis of subersic acid and makassaric acid analogues Schwab, Katerina


Concise syntheses towards derivatives of the meroterpenoids makassaric acid and subersic acid were developed. Three methods towards the development of makassaric acid were explored. The E-selective alkylation of an allyl iodide derived from sclareol was conducted, resulting in the synthesis of six new derivatives of subersic acid in 55-90% yield. Subersic acid itself was synthesized from one of these derivatives. Heck couplings were conducted on sclareol to generate four derivatives resembling makassaric acid with yields ranging from 50-74%. Conditions were screened for an alkylation reaction of a β-ketoster compound, from which 3 new makassaric acid analogues were identified in trace yields.

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