Martin D Smith

Helen Martin Old Member’s Fellow in Organic Chemistry; Professor of Organic Chemistry; Development Adviser

Teaching

I teach all aspects of organic chemistry to undergraduates at Univ and am also director of a large graduate teaching and training programme based on organic synthesis where I teach courses on total synthesis, pericyclic reactions and metal-free catalysis.

Research

I run a synthetic chemistry research group with a focus on enantioselective catalysis, the synthesis of complex molecules and the investigation and exploitation of non-covalent interactions.

ENANTIOSELECTIVE CATALYSIS: A focus of our current work is the development of catalytic enantioselective methods using chiral counterions. We have applied this approach to the synthesis of complex molecules, and demonstrated that enantioselective 5-endo-trig Michael addition reactions are not always precluded by geometric constraints (as embodied by the Baldwin rules). More recently our work has centred on approaches to control the synthesis of axially chiral molecules including axially chiral biaryls and spirobiindanones.

TOTAL SYNTHESIS OF NATURAL PRODUCTS: We are also engaged in the total synthesis of complex natural products using cascade sequences to shorten or accelerate synthetic sequences.  We have recently completed the synthesis of (-)-Gephyrotoxin and Morphine.

NON-COVALENT INTERACTIONS IN CATALYSIS AND STRUCTURE: We have built structures stabilized by hydrogen bonds such as helices, sheets and turns, and have used a designed β-turn construct to generate efficient hydrogen bonding catalysts that provide very high levels of enantioselectivity at low loadings.  We are particularly interested in the structural and catalytic influence of the C—H•••O interaction.

Selected Publications

Discovery of a Highly Selective Cell-Active inhibitor of KDM2/7, Angew. Chem. Int. Ed. 2017, DOI: 10.1002/anie.201706788

Visible Light Photocatalysis of 6π Heterocyclization, Angew. Chem. Int. Ed. 2017, 56, 9468.

Catalytic Enantioselective Synthesis of Atropisomeric Biaryls by a Cation-Directed O-Alkylation, Nature Chem. 2017, 9, 558.

A Cascade Strategy Enables a Total Synthesis of Morphine, Angew. Chem. Int. Ed. 2016, 55, 14306.

A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes, Angew. Chem. Int. Ed. 2016, 55, 13813.

Catalytic Enantioselective Synthesis of C1 and C2-Symmetric Spirobiindanones Through Counterion-Directed Enolate C-Acylation, Angew. Chem. Int. Ed. 2016, 55, 13180.

Cation-Controlled Enantio- and Diastereoselective Synthesis of Indolines: an Autoinductive Phase–Transfer Initiated 5-Endo-Trig Process, J. Am. Chem. Soc. 2015, 137, 13414.

Catalytic Enantioselective Synthesis of Indanes by a Cation-Directed 5-Endo-Trig Cyclization, Nature Chem. 2015, 7, 171.

A Cascade Strategy Enables a Total Synthesis of Gephyrotoxin, Angew. Chem. Int. Ed. 2014, 53, 13826.

Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction, Angew. Chem. Int. Ed. 2014, 53, 12822.