Enantioselective synthesis of tetracyclic quassinoid intermediates via a diene transmissive diels-alder strategy

dc.contributor.author	Tu, Noah Pui-Wai	en_US
dc.date.accessioned	2024-08-15T20:10:32Z
dc.date.available	2024-08-15T20:10:32Z
dc.date.copyright	1994	en_US
dc.date.issued	1994
dc.degree.department	Department of Chemistry
dc.degree.level	Master of Arts M.A.	en
dc.description.abstract	Starting from 2-cyclohexene-1-one 62, an enantioselective synthetic route to an optically pure tetracyclic quassinoids intermediate, compound 102, was developed. Two bulky substituents (methyl at C₄ and t-butyldimethylsilyloxy at C₃) were introduced to affect the mode of the intramolecular Diels-Alder cycloaddition to the desired face which consequently controlled the absolute stereochemistry at C₅, C₆, C₇ and C₁₀ of the tetracyclic compounds. This strategy, based on a diene-transmissive Diels-Alder cycloaddition, could be used for the enantioselective total synthesis of quassinoid bearing the same skeleton and stereochemistry at the ring junctions. In addition, the added functionalities of the methyl at C₄ and t-butyldimethyl-silyloxy at C₃ set ring A in place for the totally synthesis of Bruceantin.	en
dc.format.extent	119 pages
dc.identifier.uri	https://hdl.handle.net/1828/19942
dc.rights	Available to the World Wide Web	en_US
dc.title	Enantioselective synthesis of tetracyclic quassinoid intermediates via a diene transmissive diels-alder strategy	en_US
dc.type	Thesis	en_US

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