主讲人：Philip Wai Hong Chan（澳大利亚莫纳什大学和英国华威大学教授）
Strategies for Complex Molecule Synthesis Driven by Gold Catalysis
Philip Wai Hong Chan
School of Chemistry, Monash University, Clayton, Victoria 3800, Australia, and Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK
In this presentation, we will disclose a selection of our recent contributions toward developing gold-catalysed methodologies that are practical and of potential use in natural products and functional materials synthesis.1–3 The talk will cover the current results of an on-going program focused on designing new and efficient synthetic routes to carbo- and heterocyclic motifs of current biological and materials interest from readily accessible propargyl substrates.2 For example, we will present a synthetic method to chemoselectively prepare bicyclo［6.3.0］undeca-2,4,9,trienyl esters efficiently from Rautenstrauch rearrangement/1,5-hydride shift/8-endo-dig cyclisation of 1-ene-4,10-diynyl esters using gold catalysis (Figure 1).3 In this work, the proposed double cycloisomerisation mechanism realised the first example of a preformed or in situ generated unactivated and conformationally unrestricted all-carbon tethered 1,7-enyne to undergo an unprecedented 8-endo-dig cyclisation pathway to give the cyclooctane motif. It additionally provides a rare synthetic method in organic chemistry that can sequentially assemble both ring components of the bicyclic compound from an acyclic substrate in one step.
1) Hashmi, A. S. K.; Toste, F. D. Eds; Modern Gold Catalyzed Synthesis; Wiley-VCH: Weinheim, Germany, 2012.
2) Day, D. P.; Chan, P. W. H. Adv. Synth. Catal. 2016, 358, 1368.
3) Mathiew M.; Tan J. K.; Chan P. W. H. Angew. Chem. Int. Ed. 2018, 57, 14235.
Philip Wai Hong Chan received his Bachelor of Science (Honours) degree in chemistry from University of Bristol, UK, in 1995, and D.Phil. degree in organic chemistry from University of Oxford, UK, in 1998. He is currently the Monash-Warwick Alliance Professor of Sustainable Chemistry at Monash University, Australia and University of Warwick, UK, since 2014. His research interests lie within the broad area of sustainable homogeneous catalysis development and its applications to the synthesis of complex molecules, natural products and functional materials.
Philip Wai Hong Chan 现任澳大利亚莫纳什大学和英国华威大学教授。主要研究可持续均相催化开发及其在复合分子、天然产物和功能材料合成中的应用。1995年获得英国布里斯托尔大学化学学士学位，1998年获得英国牛津大学有机化学博士学位。