New Strategies for the Total Synthesis of Amphidinolide F and Amphidinolides C1-3

Lead Research Organisation: University of Glasgow
Department Name: School of Chemistry

Abstract

The amphidinolides are macrolide natural products extracted from symbiotic dinoflagellates of the genus Amphidinium cultivated from the Okinawan flatworms of the Amphiscolops species. To date more than 30 members of this class of natural product have been isolated, characterised and their cytotoxicity against human cancer cell lines has been reported. Although several members of this diverse group of macrolides have been shown to exhibit potent cytotoxicity and possess other biological activities, in most cases the substantial quantities of material that would be required in order to fully establish their therapeutic potential are not available.
The objective of the proposed research programme is the design and implementation of efficient total syntheses of amphidinolides C, C2, C3 and F that will provide sufficient material for full biological evaluation of these natural products and also serve as a platform for the rapid preparation of simplified analogues. New reactions and synthetic strategies will be employed to allow the syntheses of the target compounds to be accomplished in a convergent and concise manner. The intended that the synthetic route to amphidinolide F and amphidinolides C, C2, C3 will be both modular and highly convergent in order to minimise synthetic steps and maximise the overall yields of the natural products.

Publications

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Studentship Projects

Project Reference Relationship Related To Start End Student Name
EP/N509668/1 30/09/2016 29/09/2021
2305947 Studentship EP/N509668/1 02/10/2016 01/10/2020 Daniel Andrew Mills