Part II Projects

The group usually takes up to four Part II students in each academic year. We have a strong reputation for producing high quality projects that usually result in at least one publication, and several Part IIs in the Davies group have been awarded thesis prizes in recent years. A copy of our Part II Open Day poster is available here.

Our Part II projects are usually based on existing methodology within the group, covering all areas of organic synthesis including the development of novel asymmetric transformations, mechanistic investigations, total synthesis and catalysis, and often involve target based syntheses. The following sections describe several recent Part II projects, which have all resulted in publications.



The Asymmetric Synthesis of (+)-Preussin B and its Stereoisomers

Efficient de novo asymmetric syntheses of (+)-preussin B, the C(2)-epimer of (−)-preussin B, and 3-deoxy-(+)-preussin B have been developed, using the diastereoselective lithium amide conjugate addition to tert-butyl 4-phenylbut-2-enoate and the diastereoselective reductive cyclisation of γ-amino ketones as the key steps to set the stereochemistry. This work was featured on the cover of an issue of The Journal of Organic Chemistry (volume 81 issue 12) within only a few months after completion of the project. 
 

Key Publication:

  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]
     

 

The First Asymmetric Synthesis of 3-epi-Xestoaminol C

The first reported asymmetric synthesis of 3-epi-xestoaminol C was completed by a Part II student in the Davies group. The synthesis employs diastereoselective aminohydroxylation of  tert-butyl crotonate (using our lithium amide conjugate addition methodology) as the key step to set the stereochemistry. The natural product was isolated as its N,O-diacetyl derivative for ease of purification; this material was prepared in ten steps and 17% overall yield from commercially available tert-butyl crotonate. This synthesis confirms unambiguously both the assigned structure and absolute (S,S)-configuration of the natural product.
 

KeyPublication:

  1. 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]
     

 

The Asymmetric Synthesis of (−)-Codonopsinine

The total asymmetric synthesis of the natural product (−)-codonopsinine, which employed our lithium amide conjugate addition and ring-closing iodoamination reactions as the key steps, was awarded the Organic Chemistry Thesis Prize and resulted in two publications.
 

Asymmetric synthesis of (-)-codonopsinine

KeyPublications:

  1. Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (–)-codonopsinine
    Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson, J. E.; West, C. J. Tetrahedron 2012, 68, 4302
    [View Journal Page]
  2. Asymmetric synthesis of (–)-codonopsinine
    Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson, J. E.; West, C. J. Tetrahedron Lett. 2011, 52, 6477 [View Journal Page]
     


Selected Other Publications Resulting from the Work of Recent Part II Students:

  1. Pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol: concise asymmetric syntheses of (+)-trachelanthamidine, (+)-tashiromine and (+)-epilupinine
    Brambilla, M.; Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E.; Zimmer, D. Tetrahedron 201672, 7417 [View Journal Page]
  2. Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-hydroxy-β-amino esters
    Davies, S. G.; Fletcher, A. M.; Frost, A. B.; Kennedy, M. S.; Roberts, P. M.; Thomson, J. E. Tetrahedron 201672, 2139 [View Journal Page]
  3. Asymmetric syntheses of polysubstituted homoprolines and homoprolinols
    Csatayová, K.; Davies, S. G.; Figuccia, A. L. A.; Fletcher, A. M.; Ford, J. G.; Lee, J. A.; Roberts, P. M.;
    Saward, B. G.; Song, H.; Thomson, J. E. Tetrahedron 201571, 9131 [View Journal Page]
  4. The synthesis and crystal structures of two hydrogen-bonded N-oxides
    Brock, E. A.; Davies, S. G.; Hewings, D. S.; Lee, J. A.; Thompson, A. L.; Thomson, J. E. J. Chem. Crystallogr.201444, 548 [View Journal Page]
  5. 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]
  6. 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]
  7. Synthesis and crystal structures of (RS,RS,RS)- and (1RS,2RS,3SR)-3-(N-methylamino)-
    cyclohexane-1,2-diol
    Davies, S. G.; Hewings, D. S.; Lee, J. A.; Kurosawa, W.; Roberts, P. M.; Thompson, A. L; Thomson, J. E. J. Chem. Crystallogr. 201444, 30 [View Journal Page]
  8. Synthesis and crystal structures of N-aryl-N-methylaminocyclohexanols
    Cresswell, A. J.; Davies, S. G.; Hewings, D. S.; Kurosawa, W.; Lee, J. A.; Morris, M. J.; Roberts, P. M.;
    Thomson, J. E. J. Chem. Crystallogr. 201343, 646 [View Journal Page]
  9. Asymmetric synthesis of 3,4-syn- and 3,4-anti-4-amino-3-alkylpiperidines and 4-hydroxy-3-alkylpiperidines: application to the asymmetric synthesis of (+)-(3S,4R)-cisapride
    Davies, S. G.; Huckvale, R.; Lee, J. A.; Lorkin, T. J. A.; Roberts, P. M.; Thomson, J. E. Tetrahedron 201268, 3263 [View Journal Page]
  10. Ammonium-directed olefinic oxidation: kinetic and mechanistic insights
    Brennan, M. B.; Claridge, T. D. W.; Compton, R. G.; Davies, S. G.; Fletcher, A. M.; Henstridge, M. C.; Hewings, D. S.; Kurosawa, W.; Lee, J. A.; Roberts, P. M.; Schoonen, A. K.; Thomson, J. E. J. Org. Chem. 201277, 7241 [View Journal Page]
  11. Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride
    Davies, S. G.; Huckvale, R.; Lorkin, T. J. A.; Roberts, P. M.; Thomson, J. E. Tetrahedron: Asymmetry 201122, 1591 [View Journal Page]
  12. Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure
    Davies, S. G.; Fletcher, A. M.; Hughes, D. G.; Lee, J. A.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Smith, A. D.; Thomson, J. E.; Williams, O. M. H. Tetrahedron 201167, 9975 [View Journal Page]
  13. The stereodivergent aziridination of allylic carbamates, amides and sulfonamides
    Davies, S. G.; Ling, K. B.; Roberts, P. M.; Russell, A. J.; Thomson, J. E.; Woods, P. A. Tetrahedron 201066, 6806 [View Journal Page]
  14. Asymmetric synthesis of piperidines and octahydroindolizines
    Davies, S. G.; Hughes, D. G.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Smith, A. D.; Thomson, J. E.; Williams, O. M. H. Synlett 2010, 567 [View Journal Page]

 

 

 

 


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