Part 1 - Solid Phase Reactions and Part 2 - Studies Towards the Synthesis of Asterriquinone and Petromindole

Zhu, Xiuwen (2001) Part 1 - Solid Phase Reactions and Part 2 - Studies Towards the Synthesis of Asterriquinone and Petromindole. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

In part I, Barton esters were demonstrated to be excellent radical precursors for carbon-carbon bond forming reactions on solid phase. The alkyl radicals were generated photochemically from the corresponding Barton esters and underwent conjugate addition to acrylate immobilized on polystyrene and TentaGel resins. This work was carried out at the Institute of Molecule and Cell Biology, National University of Singapore.

Part II describes synthetic approaches towards several natural products. Two methods of the biomimetic synthesis of polyporic acid by condensation of two molecules of pyruvate are described in Chapter Two. A one-step procedure for the prenylation of indole in high yield under very mild and straightforward reaction conditions is introduced in Chapter Three. This method is also suitable for substituted indoles and alkylations with other allylic, benzylic and tertiary halides. A model study with tryptophan shows that the procedure is also adaptable to the core skeleton of mollenines and other alkaloid natural products. An application of the method of alkylation is shown in the last chapter. ω-Epoxygeranyl, ω-epoxyfarnesyl and ω-epoxygeranylgeranyl groups were attached to the C-3 position of indole under our established alkylation conditions. Epoxide initiated polyene cyclizations using indole as a terminator were extensively studied with these compounds.

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