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Dr Andrew L. Lawrence

Dr Andrew L. Lawrence

Lecturer in Organic Chemistry

Room 217

University of Edinburgh
Joseph Black Building
David Brewster Road
Edinburgh
EH9 3FJ

Research Interests

Total Synthesis of Natural Products, Biomimetic Chemistry, Domino Reactions

Research Overview

Our group does research in the area of natural product synthesis and the development of synthetic methodology. The aim of our research is to use nature as a source of inspiration and direction to improve and develop synthetic organic chemistry. Evolution has resulted in the highly efficient biosynthetic chemical pathways observed within living organisms. In our research we aim to harness the power of evolution by mimicking these chemical pathways.

This biomimetic approach to organic synthesis leads to a deeper understanding of how nature operates and illuminates the potential of new chemical reactions. Our biomimetic approach towards organic chemistry is primarily focused upon the synthesis of complex and biologically important natural products. When choosing our target natural products we are drawn to compounds that have extraordinary biosynthetic origins, complex molecular architectures and potent or novel biological/medicinal profiles.

Lawrence group reaction mechanism

We proposed that the unique and complex structure of the kingianin family of natural products was formed in nature through a spectacular radical cation formal Diels-Alder dimerization. We have recently completed a total synthesis of kingianins A, D and F in just ten steps following a strategy inspired by this biosynthetic speculation.

Lawrence research image

Certain phenylethanoid dimers and pseudo-dimers are assembled in nature through elegant sequences of nucleophilic addition reactions (Michael, aldol, Mannich reactions, etc.). We recently accomplished a total synthesis of incarvilleatone via a key biomimetic oxa-Michael/Michael/aldol reaction sequence.

Publications

  1. Total Synthesis and Structural Revision of the Alkaloid Incargranine B. Brown, P. D.; Willis, A. C.; Sherburn, M. S.; Lawrence, A. L.* Angew. Chem. Int. Ed. 201352, 13273-13275.
  2. Total Synthesis of Kingianins A, D and F. Drew, S. L.; Sherburn, M. S.; Lawrence, A. L. Angew. Chem. Int. Ed. 2013, 52, 4221-4224.
  3. Total Synthesis of Incarviditone and Incarvilleatone. Brown, P. D.; Willis, A. C.; Sherburn, M. S.; Lawrence, A. L.* Org. Lett. 2012, 14, 4537-4539.