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Toward the Synthesis of Rimarikiamide A

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thesis
posted on 22.11.2021, 11:48 by Asbury, Ashton Nikylla

Rimarikiamide A is a linear diterpenoid marine natural product featuring an unusual taurine structural moiety. Rimarikiamide A was isolated from the sea sponge Latrunculia brevis found in the Rimariki Islands in northern New Zealand, and was shown to elicit low μM cytotoxicity against HL-60 cells. Unfortunately, only 400 μg of rimarikiamide A was isolated from 700 g of sea sponge, making the characterisation of the two chiral centres impossible by spectroscopic means. To explore the full potential of rimarikiamide A as a therapeutic agent, the molecule must be synthesised in a stereoselective manner or from a starting material of known stereochemistry, fully characterised, and tested for biological activity. A Barbier coupling of two terpene units is required early in the proposed synthesis of Rimarikiamide A, and previous attempts have failed to generate the desired linear product. In this work, the suitability of a titanium-mediated Barbier coupling was investigated, and proved successful for the generation of the desired linear product.

History

Copyright Date

01/01/2017

Date of Award

01/01/2017

Publisher

Te Herenga Waka—Victoria University of Wellington

Rights License

Author Retains Copyright

Degree Discipline

Chemistry

Degree Grantor

Te Herenga Waka—Victoria University of Wellington

Degree Level

Masters

Degree Name

Master of Drug Discovery and Development

ANZSRC Type Of Activity code

970103 Expanding Knowledge in the Chemical Sciences

Victoria University of Wellington Item Type

Awarded Research Masters Thesis

Language

en_NZ

Victoria University of Wellington School

School of Chemical and Physical Sciences

Advisors

Keyzers, Rob