Efforts towards the total synthesis of desmethylprehelminthosporol

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Description: The main goal of this project was to synthesize desmethylprehelminthosporol, an analog of helminthosporol. A crucial objective in this synthesis is the formation of the [3.2.1]-bicyclooctane core that is a trait of these natural products. In order to synthesize the [3.2.1]-bicyclooctane core a divinylcyclopropane rearrangement, based on a Cope rearrangement, was performed on its synthetic precursor, a vinyl [3.1.0]-bicyclohexanone. This bicycle, a key intermediate, was synthesized via a modified Darzens condensation using 4-hydroxymethylcyclopent-2-enone and ethyl bromocrotonate. Synthesis of the substituted cyclopentenone is achieved through a silyl-directed Nazarov cyclization of a silylated divinylketone, following its synthesis. The research surrounding these reactions is described herein.
Language: English
Format: Degree Work