Total Synthesis

We have utilised some of the methodology developed in the group in total syntheses of a range of enantiopure compounds including natural products, their analogues and other potential therapeutic agents. 

Recently completed syntheses include (−)-turneforcidine, (+)-preussin B, (−)-nakinadine D, (−)-lupinine, (−)-fagomine, (−)-hopromalinol,(+)-pseudodistomin D, (−)-martinellic acid, (+)-pseudococaine, N,O-diacetyl-3-epi-xestoaminol C, (−)-absouline, (−)-codonopsinine, (+)-1-deoxynojirimycin, (−)-homaline, (+)-jaspine B, (−)-isoretronecanol, (−)-angustueine, and many others.

We are actively pursuing the synthesis of other natural product targets including (−)-morphine, (−)-loline, (−)-cuspareine, (−)-pseudodistomin B, (+)-simplifungin and (−)-microginin 680.



 

Key Recent Publications: 

  1. Asymmetric syntheses of (+)-preussin B, the C(2)-epimer of (–)-preussin B, and 3-deoxy-(+)-preussin B
    Buchman, M.; Csatayová, K.; Davies, S. G.; Fletcher, A. M.; Houlsby, I. T. T.; Roberts, P. M.; Rowe, S.; Thomson, J. E. J. Org. Chem. 201681, 4907 [View Journal Page]
  2. Asymmetric syntheses of (–)-hastanecine, (–)-turneforcidine and (–)-platynecine
    Brambilla, M.; Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E. Tetrahedron 201672, 4523
    [View Journal Page]
  3. Asymmetric synthesis of N,O-diacetyl-3-epi-xestoaminol C: structure and absolute configuration confirmation of 3-epi-xestoaminol C
    Archer, S. G.; Csatayová, K.; Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E. Tetrahedron Lett. 201657, 1270 [View Journal Page]
  4. Asymmetric syntheses of nakinadine D, nakinadine E and nakinadine F: confirmation of their relative (RS,SR)-configurations and proposal of their absolute (2S,3R)-configurations
    Davies, S. G.; Fletcher, A. M.; Shah, R. S.; Roberts, P. M.; Thomson, J. E. J. Org. Chem. 201580, 4017
    [View Journal Page]
  5. Concise total asymmetric syntheses of (–)-fagomine, two of its epimers, and two seven-membered
    ring congeners
    Csatayová, K.; Davies, S. G.; Fletcher, A. M.; Ford, J. G.; Klauber, D. J.; Roberts, P. M. Thomson, J. E. Tetrahedron 201571, 7170 [View Journal Page]
  6. The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes
    Davies, S. G.; Fletcher, A. M.; Foster, E. M.; Houlsby, I. T. T.; Roberts, P. M.; Schofield, T. M.; Thomson,
    J. E. Org. Biomol. Chem. 201412, 9223 [View Journal Page]
  7. An efficient asymmetric synthesis of (–)-lupinine
    Davies, S. G.; Fletcher, A. M.; Foster, E. M.; Houlsby, I. T. T.; Roberts, P. M.; Schofield, T. M.; Thomson, J. E.Chem. Commun. 201450, 8309 [View Journal Page]
  8. A diastereodivergent strategy for the synthesis of (–)-martinellic acid and (–)-4-epi-martinellic acid
    Davies, S. G.; Fletcher, A. M.; Lee, J. A.; Lorkin, T. J. A.; Roberts, P. M.; Thomson, J. E. Tetrahedron 201369, 9779 [View Journal Page]
  9. Asymmetric synthesis of (–)-martinellic acid
    Davies, S. G.; Fletcher A. M.; Lee, J. A.; Lorkin, T. J. A.; Roberts, P. M.; Thomson, J. E. Org. Lett. 201315, 2050 [View Journal Page]
  10. Asymmetric synthesis of (–)-absouline
    Davies, S. G.; Fletcher, A. M.; Lebée, C.; Roberts, P. M.; Thomson, J. E.; Yin, J. Tetrahedron 201369, 1369 [View Journal Page]
  11. Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination
    Brock, E. A.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson, J. E. Org. Lett. 2012, 14, 4278
    [View Journal Page]
  12. Polysubstituted piperidines via iodolactonisation: application to the asymmetric synthesis of
    pseudodistomin D
    Davies, S. G.; Fletcher, A. M.; Lee, J. A.; Roberts, P. M.; Russell, A. J.; Taylor, R. J.; Thomson, A. D.; Thomson, J. E. Org. Lett. 2012, 14, 1672 [View Journal Page]
  13. Absolute configuration assignment by asymmetric syntheses of the homalium alkaloids (–)-(R,R,R)-hoprominol and (–)-(4'S,4''R,2'''R)-hopromalinol
    Davies, S. G.; Lee, J. A.; Roberts, P. M.; Stonehouse, J. P.; Thomson, J. E. J. Org. Chem. 201277, 9724
    [View Journal Page]

 

 

 

 

 


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