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- W1675505533 abstract "The thesis presents the first enantioselective synthesis of the proposed structure of sclerophytin F and consequently, the first total synthesis of a cladiellin family member having the S-configuration at the C-3 stereocentre. Three novel enantioselective routes are described to access a pivotal intermediate; then, the synthesis follows three key steps: i) radical-mediated cyclisation, ii) oxonium ylide formation and [2,3]-sigmatropic rearrangement, iii) Diels-Alder cycloaddition to deliver the core of the natural product. The novelty of the route relies on the introduction of the C-3 methyl group at an early stage of the synthesis. As anticipated, the presence of this extra methyl had significant influence on many transformations. Finally, the elaboration of the core to meet the proposed structure was completed. Unfortunately, none of the recorded data matched those originally reported for the natural compound. A further three stereoisomers were synthesised but their data also did not match the original." @default.
- W1675505533 created "2016-06-24" @default.
- W1675505533 creator A5072744091 @default.
- W1675505533 date "2014-01-01" @default.
- W1675505533 modified "2023-09-27" @default.
- W1675505533 title "Total synthesis of the proposed structure of sclerophytin F and structure re-evaluation" @default.
- W1675505533 hasPublicationYear "2014" @default.
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