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Discussion Meeting Mechanisms Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid Clark, J. S.; Baxter, C. A.; Dossetter, A. G.; Poigny,

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Presentation on theme: "Discussion Meeting Mechanisms Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid Clark, J. S.; Baxter, C. A.; Dossetter, A. G.; Poigny,"— Presentation transcript:

1 Discussion Meeting Mechanisms Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid Clark, J. S.; Baxter, C. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. January 22 nd, 2008 Université de Montréal

2 Retrosynthetic Analysis Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 2

3 Synthesis of Allylbromide Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 3

4 Mechanism of Allylsilane Formation (Miguel) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 4

5 Synthesis of Diazoketone Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 5

6 Oxidative Cleavage Mechanism (Sébas) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 6

7 Grignard Addition Mechanism (Angélique) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 7

8 Synthesis of Diazoketone Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 8

9 Oxidation Mechanism (G. Pelletier) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64,

10 Oxidation Mechanism Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64,

11 Synthesis of Second Diazoketone Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 11

12 Synthesis of Second Diazoketone (Vincent) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 12

13 Synthesis of Second Diazoketone (Vincent) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 12

14 Diazoketone Key Cyclization (Maude) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 13

15 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Diazoketone Key Cyclization 14

16 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Oxygen Insertions 15

17 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Oxygen Insertions (Fred) 16

18 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Al-Mediated Rearrangement (Louis) 17

19 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Al-Mediated Rearrangement 18

20 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Final Cyclization 19

21 Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Most Advanced Precursor 20


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