Gregory Dake

Associate Professor

Office: Chemistry A341
Office Phone: (604) 822-9121
Lab(s): Chemistry A303/A304
Lab Phone(s): (604) 822-0422

FAX: (604) 822-2847
Email: gdake@chem.ubc.ca

Curriculum Vitae: B.Sc.(Hons.), British Columbia (1992); Ph.D. Stanford University (Barry M. Trost, 1998); Postdoctoral, Columbia University (Gilbert Stork, 1998-1999)

Organic: New methods for organic synthesis; metal-mediated or catalyzed processes; tandem reactions; asymmetric catalysis; synthesis and chemistry of biologically active and/or structurally interesting natural products.

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Research/Teaching Interests

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.