Synthetic endeavours into natural products: the synthesis of monosporascone and the antrocamphins

Kathryn Punch

Research output: ThesisDoctoral Thesis

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Abstract

The total synthesis of natural products continues to be a key area of interest for synthetic organic chemists. Given the challenges associated with isolating and purifying the compounds and the difficulty in obtaining sufficient quantities from the natural sources, total synthesis is often essential to provide access to enough material for extensive biological investigations. Additionally, total synthesis is recognised as an excellent proving ground for synthetic methodology and allows the chemist to "edit" the compound, removing areas responsible for potential toxicity and adding structural features that may increase activity and viability as a therapeutic agent. This thesis comprises two parts: the total synthesis of natural products from two different families of compounds. Part 1 looks at the naphtho[2,3-c]furan-4,9-dione family, with part 2 focusing on the synthesis of some novel alkynylbenzenoids. Chapter 1 is a brief introduction about natural product synthesis and the aims of this research are described herein. Chapter 2 gives a comprehensive introduction to the quinone and furan classes of compounds and then discusses the naphtho[2,3-c]furan-4,9-diones, also known as isofuranonaphthoquinones, represented by the parent compound 44. These compounds have received much attention because this skeleton is found in many natural products, which exhibit a diverse range of biological activities, including antioxidant, antibacterial and anticancer properties. Isofuranonaphthoquinones with a 1,3-unsubstituted furan ring and a 5,7-substitution pattern have not been previously synthesised. The first total synthesis of two such natural products, monosporascone (1), and dihydromonosporascone (2), will be described. Chapter 3 will discuss a related synthetic route that provides access to the naphtho[2,3- c]furan-4(9H)-one skeleton (199). The synthesis of a novel ortho-dibromide (218) as part of an alternative route to 1 will also be discussed.
Original languageEnglish
QualificationDoctor of Philosophy
Publication statusUnpublished - 2010

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