Nicolas Gaeng Group seminar – LSPN – 30/04/15. Structures with multiple rings connected through one atom Nomenclature proposed by Adolf Baeyer in 1900.

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Presentation transcript:

Nicolas Gaeng Group seminar – LSPN – 30/04/15

Structures with multiple rings connected through one atom Nomenclature proposed by Adolf Baeyer in 1900 Challenging quaternary carbon center Introduction – spirocyclic compounds 1-bromospiro[4.5]decane Baeyer, A. Berichte der deutschen chemischen Gesellschaft 1900, 33, '-methylspiro[indoline-3,3'-pyrrolidin]-2-one Horsfiline

Spirooxindole: Isolated from Apocynaceae and Rubiacae  Biological activites Spiroindoline: Isolated from Strychnos  Antitumor activities Main families Vinblastine Bindra, J. S. In The Alkaloids 1973, 14, 84. (-)-spirotryprostatin B

General consideration Racemization through a retro-Mannich reaction

One of the most common methods Usual reagents: OsO 4, Pb(OAc) 4, t BuOCl, NBS, Na 2 WO 4 From tetrahydro-β-carbolines (tryptoline) Oxidative Rearrangements Bischler-NapieralskiPictet-Spengler

Oxidative Rearrangements Cook’s studies on alstonisine Cook, J. M. et al. J. Org. Chem. 1995, 60, 120. Cook, J. M. et al. Org. Lett. 2002, 4, Cinchona type ligand pinacol convex vs concave

Oxidative Rearrangements Cook’s synthesis of alstonisine Cook, J. M. et al. J. Org. Chem. 1995, 60, 120. Cook, J. M. et al. Org. Lett. 2002, 4, Pearlman’s cat.: Pd(OH) 2 /C, H 2

Oxidative Rearrangements Danishefsky’s synthesis of spirotryprostatin A Danishefsky, S. J. et al. J. Am. Chem. Soc. 1999, 121, 2147.

Oxidative Rearrangements Williams’ studies on paraherquamide Williams, R. M. et al. Tetrahedron Lett. 1989, 30, 5575.

Oxidative Rearrangements Williams’ synthesis of paraherquamide A Williams, R. M. et al. J. Am. Chem. Soc. 2003, 125,

1,3-dipolar cycloaddition Waldmann’s studies based on spirotryprostatin Waldmann, H. et al. Nat. Chem. 2010, 2, 735.

Azomethine Ylide Cycloaddition Palmisano’s synthesis of (-)-horsfiline Palmisano, G. J. et al. J. Org. Chem. 2001, 66, % de

Asymmetric Addition-Elimination Fuji’s synthesis of (-)-horsfiline Fuji, K. L. et al. J. Am. Chem. Soc. 1989, 111, Fuji, K. L. et al. J. Org. Chem. 1999, 64, >99% ee

Pd-Catalyzed Heck Reactions Overman, L. E. et al. J. Org. Chem. 1989, 54, Overman, L. E. et al. Angew. Chem. Int. Ed. 2000, 39, Overman’s synthesis of (-)-spirotryprostatin B

Pd-Catalyzed Heck Reactions Overman, L. E. et al. J. Am. Chem. Soc. 2005, 127, Overman’s synthesis of gelsemine

Pd-Catalyzed Allylic Alkylation Trost’s synthesis of (+)-horsfiline Trost, B. M. et al. Org. Lett. 2006, 8, 2027.

Ring Expansion Carreira’s synthesis of (-)-spirotryprostatin B Carreira, E. M. et al. Angew. Chem. Int. Ed. 2003, 42, 694.

Mannich Reaction Danishefsky’s synthesis of (-)-spirotryprostatin B Danishefsky, S. J. et al. Angew. Chem. Int. Ed. 2000, 39, 2175.

Retro-Mannich Reaction White’s synthesis of elacomine White, J. D. et al. J. Org. Chem. 2010, 75, hµ [2+2] retro-Mannich

Retro-Mannich Reaction White’s synthesis of elacomine White, J. D. et al. J. Org. Chem. 2010, 75, oxidative rearrangement

Conclusion Pros Variety of methods Metal-catalyzed processes promising Many more to come… Cons Selectivity issue Auxiliary – not atom economic

Outlook Trost, B. M. et al. J. Am. Chem. Soc. 2007, 129, Trost, B. M. et al. J. Am. Chem. Soc. 2007, 129, Trost’s synthesis of marcfortine B

Outlook Zhu, J. et al. Chem. Eur. J. 2007, 13, 961. Zhu, J. et al. Synlett 2009, 18, Zhu’s synthesis of horsfiline

Thank you for your attention