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Title: Towards the total synthesis of amphidinolide C
Author: Yang, Guang
ISNI:       0000 0004 2736 7697
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2013
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Amphidinolide C is a macrolactone possessing two trans-2,5 substituted tetrahydrofurans embedded in the ring, isolated from the inner cells of acoel flatworms that live on algae and seaweed in the coral reefs of Okinawa. Amphidinolide C possesses complex molecular architecture and this combined with its potent biological activity make it an alluring target for synthesis. Herein, is presented the convergent synthetic route towards the total synthesis of amphidinolide C, including the enantioselective total synthesis of two key intermediates C1–C17 and C18–C34 fragments. The key transformations in the synthetic route of C1–C17 fragment include intramolecular conjugate addition of an oxygen nucleophile to obtain the trans-2,5 tetrahydrofuran (C1–C8 subunit), stereoselective boron-mediated aldol condensation, E-selective HWE olefination of a ketone followed by regioselective hydrostannylation of an enyne to give the desired diene system. Lastly, C1–C17 fragment was complete by nucleophilic addition of aldehyde with a vinylic anion. Important features of the synthesesis of the C18–C34 fragment include kinetic resolution under Sharpless asymmetric epoxidation conditions to furnish the enantionmericly pure alcohol, Sonogashira coupling followed by Red-Al reduction of the enyne system to obtain the E,E-diene system.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry