Exploring a Symmetry Based Logic for Palau'amine Synthesis

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Exploring a Symmetry Based Logic for Palau'amine Synthesis

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Title: Exploring a Symmetry Based Logic for Palau'amine Synthesis
Author: Li, Qingyi
Abstract: Palau'amine is a natural product originally isolated in 1993 from the marine sponge Stylotella aurantium. It is reported to posess impressive biological activities, including: antifungal, antibacterial, and antineoplastic characters. Moreover, it is a strong immunosuppressant (IC50<18ng/mL, allogenic lymphocyte reaction). The molecule has a complex polycyclic structure having a contiguous array of eight stereogenic centers. It is unusually rich in heteroatoms. A recent revision of its relating stereochemistry has brought further attention to this fascinating molecule. The current strategy of our group features a chlorination initiated cascade process on a symmetric precursor that assembles the skeleton of palau'amine with in a single operation. A symmetric bisalkylidene precursor for this process was synthesized. During the process, two new methodologies were developed: a titanocene dichloride mediated regioselective and stereoselective dimerization of heterocyclic dineolates; and a chemoselective Rh(I) carbene complexes catalyzed conjugation hydrosilylation of enamides. Our core idea was subsequently validated by the formation of the spirocyclopentane motif in palau'amine by an electrophilic halogen induced desymmetrization.
URI: http://hdl.handle.net/2152.5/282
Date: 2008-05-13

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