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Type: Theses
Title: Biomimetic total synthesis of natural products
Author: Lam, Hiu Chun
Issue Date: 2018
School/Discipline: School of Physical Sciences
Abstract: This thesis describes several syntheses of natural products. The overall synthetic approach is to mimic how these secondary metabolites could be derived in Nature, where we aim to gain insights into the biosynthesis of these natural products from the syntheses. The first synthesis of hyperjapones A-I was achieved by an oxidative hetero-Diels-Alder reaction. The transformation of hyperjapone A to hyperajaponols A and C was achieved via an epoxidation and an acid-catalysed rearrangement cascade reaction, forming 4 stereocenters and 2 rings in 1 step. The first synthesis of verrubenzospirolactone was achieved from a Diels-Alder reaction of the polyene in water. Capillobenzopyranol, the proposed biosynthetic precursor of verrubenzospirolactone was also synthesized and converted into verrubenzospirolactone by mirroring our proposed biosynthetic pathway. The first synthesis of rhodonoids C and D, and murrayakonine D was achieved. The key biomimetic step was the acid catalysed rearrangement of an epoxide, forming 3 stereocenters and 2 rings in 1 step. The biomimetic total synthesis of yezo’otogirin C was achieved via an oxidative radical cyclization cascade reaction, forming 2 rings, 2 stereocenters, 1 C=C bond, 1 C-C bond and 1 C-O bond in 1 step.
Advisor: George, Jonathan
Dissertation Note: Thesis (Ph.D.) -- University of Adelaide, School of Physical Sciences, 2018.
Keywords: total synthesis
natural products
organic chemistry
Provenance: This electronic version is made publicly available by the University of Adelaide in accordance with its open access policy for student theses. Copyright in this thesis remains with the author. This thesis may incorporate third party material which has been used by the author pursuant to Fair Dealing exceptions. If you are the owner of any included third party copyright material you wish to be removed from this electronic version, please complete the take down form located at:
DOI: 10.25909/5b3c5b573837c
Appears in Collections:Research Theses

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