个人简介

B.Sc.(Hons.), British Columbia (1992); Ph.D. Stanford University (Barry M. Trost, 1998); Postdoctoral, Columbia University (Gilbert Stork, 1998-1999). 2010 Science Undergraduate Society Teaching Excellence Award 2012 University of British Columbia Killam Teaching Prize

研究领域

Chemical Synthesis; Organic Chemistry

My research program is directed towards the creation, understanding and application of methods for organic synthesis. The approach is to use metals to catalyze or mediate organic reactions which would be difficult or impossible using "classical" methods; to sequence reactions in situ in order to carry out more than one transformation in a single reaction vessel; and to discover new methods to produce chiral organic molecules in a highly (relatively and/or absolutely) stereocontrolled manner. The ultimate goal in the development of new methods is their incorporation in the challenging context of total synthesis of bioactive or structurally interesting molecules (usually natural products). There are three topics of active investigation in my lab at the moment. 1) Rearrangement Reactions. An ongoing interest in our group is the use of structural rearrangements to generate tertiary and quaternary chirality carbon centers. For example, we are currently investigating (alpha)-alkoxy imine or (alpha)-alkoxy iminium ion semipinacol rearrangement reactions: a) a Bronsted acid promoted ring expansion of small rings and b) a Lewis acid promoted semipinacol rearrangement of (alpha)-siloxy epoxides. These reactions generate azaspirocyclic ketones with high yields and stereoselectivities. We have completed a synthesis of fasicularin using a ring-expansion reaction as a key step. We are currently using these methods in synthetic approaches towards the structurally interesting alkaloids such as halichlorine, pinnaic acid and the cylindricine family. 2) Terpene Synthesis. To meet the challenge of a total synthesis of a natural product, synthetic organic chemists are often compelled to discover new reactions or new contexts for "literature" reactions. In our case, our synthetic work towards nitiol (a sesterterpenoid that promotes production of interleukin-2) has generated several lines of study. One topic in development is a new technique for constructing macrocycles (large rings). We believe this technique can be applied to other macrocyclic natural products beyond nitiol. 3) Metal-Catalyzed Annulations. We have discovered Pt (II) and Ag (I) catalyzed pathways for the cyclizations of enecarbamates and enesulfonamides onto alkynes. These reactions can proceed in high yield (>90%) at low catalyst loads (1-3 mol%). These reactions are sufficiently mild that they have been used as the first reaction within a tandem multibond-forming sequence. This exciting process looks like it could be quite useful for the construction of complex heterocyclic ring systems such as the one embedded within nakadomarin A. Students trained in synthetic organic chemistry think deeply about the relationships between molecular structure, chemical reactivity and reaction mechanism. Thus, they are typically well poised to pursue a number of avenues of scientific inquiry in academia and industry later in their careers. I encourage you to browse our "group" web page for further information regarding our research interests, the members of our research group, as well as the Department of Chemistry at the University of British Columbia.

近期论文

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Serin, S. C. ; Patrick, B. O. ; Dake, G. R. ; Gates, D. P. Reaction Of An Enantiomerically Pure Phosphaalkene-Oxazoline With Mem Nucleophiles (M = Li And Mgbr): Stereoselectivity And Noninnocence Of The P-Mesityl Substituent. ORGANOMETALLICS 2014, 33, 7215-7222.BibTex Castillo-Contreras, E. B. ; Stahl, A. M. ; Dake, G. R. Annulated Isoxazoles Via [3+2] Cycloaddition Of Alkenyl Bromides And Oximoyl Chlorides And Ag(I) Promoted Elimination. JOURNAL OF ORGANIC CHEMISTRY 2014, 79, 7250-7255.BibTex Castillo-Contreras, E. B. ; Dake, G. R. Dmap Promoted Tandem Addition Reactions Forming Substituted Tetrahydroxanthones. ORGANIC LETTERS 2014, 16, 1642-1645.BibTex 2013 Vilin, Y. Y. ; Nunez, J. - J. ; Kim, R. Y. ; Dake, G. R. ; Kurata, H. T. Paradoxical Activation Of An Inwardly Rectifying Potassium Channel Mutant By Spermine: ``(B)Locking'' Open The Bundle Crossing Gate. MOLECULAR PHARMACOLOGY 2013, 84, 572-581.BibTex Sala-Rabanal, M. ; Li, D. C. ; Dake, G. R. ; Kurata, H. T. ; Inyushin, M. ; Skatchkov, S. N. ; Nichols, C. G. Polyamine Transport By The Polyspecific Organic Cation Transporters Oct1, Oct2, And Oct3. MOLECULAR PHARMACEUTICS 2013, 10, 1450-1458.BibTex Loosley, B. C. ; Andersen, R. J. ; Dake, G. R. Total Synthesis Of Cladoniamide G. ORGANIC LETTERS 2013, 15, 1152-1154.BibTex 2012 Dake, G. R. Enamides And Related Functional Groups As Nucleophilic Components In Ring-Forming Processes Catalyzed By Electrophilic Metal Salts. SYNLETT 2012, 814-824.BibTex Dugal-Tessier, J. ; Serin, S. C. ; Castillo-Contreras, E. B. ; Conrad, E. D. ; Dake, G. R. ; Gates, D. P. Enantiomerically Pure Phosphaalkene-Oxazolines (Phak-Ox): Synthesis, Scope And Copolymerization With Styrene. CHEMISTRY-A EUROPEAN JOURNAL 2012, 18, 6349-6359.BibTex 2010 Dugal-Tessier, J. ; Dake, G. R. ; Gates, D. P. Chiral Phosphaalkene-Oxazoline Ligands For The Palladium-Catalyzed Asymmetric Allylic Alkylation. Organic Letters 2010, 12, 4667 - 4669.BibTex Kozak, J. A. ; Patrick, B. O. ; Dake, G. R. Gold(I)-Catalyzed Intramolecular Tandem Addition/friedel-Crafts Reactions Between Acyclic Enamides And 1-Arylalkynes. Journal of Organic Chemistry 2010, 75, 8585 - 8590.BibTex Dugal-Tessier, J. ; Kuhn, P. - S. ; Dake, G. R. ; Gates, D. P. Synthesis Of Functional Phosphines With Ortho-Substituted Aryl Groups: 2-Rc6H4Ph2 And 2-Rc6H4P(Sime3)2 (R = 2-I-Pr- Or 2-T-Bu-). Heteroatom Chemistry 2010, 21, 265 - 270.BibTex Dugal-Tessier, J. ; Kuhn, P. - S. ; Dake, G. R. ; Gates, D. P. Synthesis Of Functional Phosphines With Ortho-Substituted Aryl Groups: 2-Rc6H4Ph2 And 2-Rc6H4P(Sime3)2 (R = 2-I-Pr- Or 2-T-Bu-). [Erratum To Document Cited In Ca153:260428]. Heteroatom Chemistry 2010, 21, 355 - 360.BibTex 2009 Kozak, J. A. ; Dodd, J. M. ; Harrison, T. J. ; Jardine, K. J. ; Patrick, B. O. ; Dake, G. R. Enamides And Enesulfonamides As Nucleophiles: Formation Of Complex Ring Systems Through A Platinum(Ii)-Catalyzed Addition/friedel-Crafts Pathway. Journal of Organic Chemistry 2009, 74, 6929-6935.BibTex 2008 Dake, G. R. ; Fenster, E. E. ; Patrick, B. O. A Synthetic Approach To The Fusicoccane A-B Ring Fragment Based On A Pauson-Khand Cycloaddition/norrish Type 1 Fragmentation. Journal of Organic Chemistry 2008, 73, 6711-6715.BibTex Hurley, P. B. ; Dake, G. R. Synthetic Studies Toward Halichlorine: Complex Azaspirocycle Formation With Use Of An Nbs-Promoted Semipinacol Reaction. Journal of Organic Chemistry 2008, 73, 4131-4138.BibTex Dugal-Tessier, J. ; Dake, G. R. ; Gates, D. P. Chiral Ligand Design: A Bidentate Ligand Incorporating An Acyclic Phosphaalkene. Angewandte Chemie-International Edition 2008, 47, 8064-8067.BibTex Kozak, J. A. ; Dake, G. R. Total Synthesis Of (+)-Fawcettidine. Angewandte Chemie-International Edition 2008, 47, 4221-4223.BibTex 2007 Harrison, T. J. ; Patrick, B. O. ; Dake, G. R. Platinum(Ii)-Catalyzed Cyclizations Forming Quaternary Carbon Centers, Using Enesulfonamides, Enecarbamates, Or Enamides As Nucleophiles. Organic Letters 2007, 9, 367-370.BibTex Dugal-Tessier, J. ; Dake, G. R. ; Gates, D. P. P,n-Chelate Complexes Of Pd(Ii) And Pt(Ii) Based On A Phosphaalkene Motif: A Catalyst For The Overman-Claisen Rearrangement. Organometallics 2007, 26, 6481-6486.BibTex