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Professor Ian Paterson FRSE FRS

Portrait of ip100

Research in the group ranges across the total synthesis of biologically active natural products and structural analogues to the discovery and development of new synthetic methods.

Stereocontrolled Synthesis of Bioactive Natural Products and Structural Analogues

Representative targets include rare anticancer polyketides of both marine and terrestrial origin such as 1-4 below. For example, dictyostatin (1) shares the same microtubule-stabilising mechanism as the clinically important anticancer drug Taxol, while spirastrellolide A (2) is a potent inhibitor of protein phosphatase 2A. Likewise, chivosazole A (3) and reidispongiolide A (4) are novel actin-interacting macrolides isolated from myxobacteria and marine sponges respectively, which also represent challenging synthetic targets. In all these cases, the initial uncertainty over the stereochemistry, combined with their natural scarcity, has adversely affected their development. Efficient and flexible synthetic routes for the modular construction of these and other complex polyketide natural products are being pursued to establish their full configurations and provide a sustainable supply for detailed biological evaluation. A parallel objective is to design simplified analogues and hybrids that retain the exceptional cancer cell growth inhibitory properties whilst increasing their synthetic accessibility.

New Synthetic Methods

There is a need for new and more efficient methods of synthesis, particularly ones that achieve high levels of stereochemical control, where the development of asymmetric aldol methodology is of particular interest. These new methods are being applied to the synthesis of a wide variety of biologically important natural products.

 

Selected Publications

  • Dictyostatin and hybrids with discodermolide and taxol. Chem. Asian J. (2011), 6, 459; Tetrahedron (2010), 66, 6534
  • Spirastrellolide A. Angew. Chem. Int. Ed. (2012), 51, 2749; Org. Biomol. Chem.  (2012), 10, 5861 and 5873
  • Polyketide natural products as anticancer drug candidates. Org. Lett.  (2013), 15, 3118; Angew. Chem. Int. Ed. (2013), 52, 6517; Angew. Chem. Int. Ed. (2011), 50, 3219Curr. Opin. Drug Discov. Devel. (2010), 13, 777
  • Natural product synthesis using asymmetric aldol reactions. Angew. Chem. Int. Ed. (2013), 52, 9097

Publications

Total synthesis of the antimitotic marine macrolide (-)-leiodermatolide
I Paterson, KK Ng, S Williams, DC Millican, SM Dalby – Angew Chem Int Ed Engl (2014) 53, 2692
The Impact of the Mukaiyama Aldol Reaction in Total Synthesis
SB Kan, KK Ng, I Paterson – Angew Chem Int Ed Engl (2013) 52, 9097
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications
KR Brunden, NM Gardner, MJ James, Y Yao, JQ Trojanowski, VM-Y Lee, I Paterson, C Ballatore, SAB III – ACS Medicinal Chemistry Letters (2013) 4, 886
Total synthesis of aplyronine C.
I Paterson, SJ Fink, LY Lee, SJ Atkinson, SB Blakey – Organic Letters (2013) 15, 3118
Total synthesis of (+)-spirastrellolide A methyl ester: Challenges and discoveries
I Paterson, P Maltas, EA Anderson – Pure and Applied Chemistry (2013) 85, 1133
Total Synthesis of (-)-Rhizopodin
SM Dalby, J Goodwin-Tindall, I Paterson – Angew Chem Int Ed Engl (2013) 52, 6517
Studies toward the total synthesis of madeirolide A
GW Haslett, CI MacGregor, SP Fearnley, I Paterson – ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY (2013) 245
Studies towards the total synthesis of Leiodermatolide
KK-H Ng, S Williams, I Paterson – ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY (2013) 245
Total synthesis of alotaketal A
M Xuan, I Paterson, S Dalby – ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY (2013) 245
Synthesis of the C1-C11 western fragment of madeirolide A.
I Paterson, GW Haslett – Organic Letters (2013) 15, 1338
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Research Group

Research Interest Group

Telephone number

01223 336407
01223 762018 (fax)

Email address

ip100@cam.ac.uk