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Séminaire Chimie ED459

Synthetic studies on polypropionates

Prof. Dale E. Ward (Department of Chemistry, University of Saskatchewan, Saskatoon, Canada)

publié le , mis à jour le

Le Jeudi 16 Octobre 2008
Salle de cours SC-16.01 (UM2)

We have been developing the essential elements of a general strategy for the rapid assembly of stereochemically diverse hexapropionate synthons as illustrated below. Ideally, one would be able to selectively access any of the 36 possible stereoisomers in one or two steps from readily available and inexpensive precursors. To achieve this objective requires aldol reactions with versatile diastereoselectivity that proceed with (dynamic) kinetic resolution. The rationale design of such reactions has allowed this goal to be partially realized (22 stereoisomers available in 2-4 steps). Applications to various polypropionate synthetic targets are possible and recent progress will be presented.

Figure 1

References :
(a) Ward, D. E. ; Sales, M. ; Man, C. C. ; Shen, J. ; Sasmal, P. K. ; Guo, C. J. Org. Chem. 2002, 67, 1618- 1629.
(b) Ward, D. E. ; Jheengut, V. ; Akinnusi, O. T. Org. Lett. 2005, 7, 1181-1184.
(c) Ward, D. E. ; Gillis, H. M. ; Akinnusi, O. T. ; Rasheed, M. A. ; Saravanan, K. ; Sasmal, P. K. Org. Lett. 2006, 8, 2631- 2634.
(d) Ward, D. E. ; Jheengut, V. ; Beye, G. E. J. Org. Chem. 2006, 71, 8989-8992.
(e) Ward, D. E. ; Beye, G. E. ; Sales, M. ; Alarcon, I. Q. ; Gillis, H. M. ; Jheengut, V. J. Org. Chem. 2007, 72, 1667-1674.
(f) Jheengut, V. ; Ward, D. E. J. Org. Chem. 2007, 72, 7805-7808.

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