Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity

Arnold, Robert

Bioinspired Synthesis of Illicium-Derived Neolignans and their Neurological Activity

Publication Date

August 4, 2021

Creator

Arnold, Robert

Abstract

Illicium-derived neolignans present a wealth of structurally diverse species that arise initially from the oxidative phenolic coupling of common unit chavicol whereby it is proposed that intermediates can also undergo oxa-1,4-additions, oxidations, and dehydrating transformations. More recently, Illicium-derived neolignans have been tested for their neurological benefits in the promotion of growth and protection of developing neurons. This thesis presents a bioinspired approach for the total synthesis of simonsol C, simonsol F (previously unnamed) and simonsol G (previously unnamed), as well as their respective biomimetic transformations to simonsinol, macranthol and honokiol via plausible hydroxydienone intermediates. From simonsol F, the total synthesis of fargenin, simonsol E, simonsin A and two further possibly over-looked natural products epi-simonsol E and epi-simonsin A are described. Studies towards the synthesis of two possible diastereoisomers of fargenone A, “bowl” and “ladder” are presented. Efforts have begun towards an enantioselective synthesis of simonsol F. Illicium-derived neolignans, intermediates from synthesis and purposefully modified derivatives have been tested in an SAR study on the promotion of axon growth of primary cultured mouse cortical neurons.

Item Type

ethesis

Thesis Type

PhD

Supervisors

Denton, Ross

Keywords

neolignans

lignans

biosynthesis

Subjects (LC)

QD Chemistry::QD241 O...

Associated Schools / Departments

School of Chemistry

eprints ID

64407

UoN Repository URI

https://repository.nottingham.ac.uk/handle/123456789/61155

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Name

Neolignans - Robert Arnold.pdf

Type

Full-text

Description

Examined. Thesis

Size

15.84 MB

Format

Adobe PDF

Checksum (MD5)

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Name

Neolignans - Robert Arnold - Supporting NMR Spectra.pdf