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Conference Paper: Synthesis of the core of welwistatin using a diazoketone rearrangement
Title | Synthesis of the core of welwistatin using a diazoketone rearrangement |
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Authors | |
Issue Date | 2013 |
Citation | The 8th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-8), Osaka, Japan, 25-28 November 2013. How to Cite? |
Abstract | We have studied and developed the rearrangement of fused bicyclic α-diazo-β-hydroxyketones in the presence of rhodium catalysts, for the synthesis of a range of bicyclo[m.n.1]alkanediones, which constitute the frameworks of many polycyclic natural products. We have rationalized the migratory aptitudes of the substituents by stereoelectronic effects. We have proceeded to investigate the scope and limitations of this methodology by applying this reaction as a key step in a synthetic study of the bicyclo[4.3.1] core of welwistatin, a natural product isolated from the cyanobacteria Hapalosiphon welwitschii. Welwistatin is a potent antagonist of P-glycoprotein pump and could reverse multiple drug resistance of cancers. Our progress in this synthetic effort will be presented. |
Persistent Identifier | http://hdl.handle.net/10722/201190 |
DC Field | Value | Language |
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dc.contributor.author | Chiu, P | - |
dc.contributor.author | Lam, SM | - |
dc.date.accessioned | 2014-08-21T07:17:24Z | - |
dc.date.available | 2014-08-21T07:17:24Z | - |
dc.date.issued | 2013 | - |
dc.identifier.citation | The 8th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-8), Osaka, Japan, 25-28 November 2013. | - |
dc.identifier.uri | http://hdl.handle.net/10722/201190 | - |
dc.description.abstract | We have studied and developed the rearrangement of fused bicyclic α-diazo-β-hydroxyketones in the presence of rhodium catalysts, for the synthesis of a range of bicyclo[m.n.1]alkanediones, which constitute the frameworks of many polycyclic natural products. We have rationalized the migratory aptitudes of the substituents by stereoelectronic effects. We have proceeded to investigate the scope and limitations of this methodology by applying this reaction as a key step in a synthetic study of the bicyclo[4.3.1] core of welwistatin, a natural product isolated from the cyanobacteria Hapalosiphon welwitschii. Welwistatin is a potent antagonist of P-glycoprotein pump and could reverse multiple drug resistance of cancers. Our progress in this synthetic effort will be presented. | - |
dc.language | eng | - |
dc.relation.ispartof | International Conference on Cutting-edge Organic Chemistry in Asia, ICCEOCA-8 | - |
dc.relation.ispartof | 第8回 アジア最先端有機化学国際会議 | - |
dc.title | Synthesis of the core of welwistatin using a diazoketone rearrangement | - |
dc.type | Conference_Paper | - |
dc.identifier.email | Chiu, P: pchiu@hku.hk | - |
dc.identifier.authority | Chiu, P=rp00680 | - |
dc.identifier.hkuros | 232036 | - |