Formal total synthesis of enantiopure tricyclic (s)-myrmicarin alkaloids 217, 215A and 215B

Heterocycles

Volumn 81, Issue 11, 2010, Pages 2523-2537

  Santarem, Marco ^a   Vanucci Bacqué, Corinne ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650089855     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-12010     Document Type: Article

References (14)

1. F. Schröder, S. Franke, W. Francke, H. Baumann, M. Kaib, J. M. Pasteels, and D. Daloze, Tetrahedron, 1996, 52, 13539.
2. For previous total synthesis of racemic M217 see: a) F. Schröder and W. Francke, Tetrahedron, 1998, 54, 5259. For previous total and formal syntheses of nonracemic myrmicarins see
3. B. Sayah, N. Pelloux-Léon, and Y. Vallée, J. Org. Chem., 2000, 65, 2824;
4. B. Sayah, N. Pelloux-Léon, A. Milet, J. Pardillos-Guindet, and Y. Vallée, J. Org. Chem., 2001, 66, 2522;
5. R. Settambolo, G. Guazzelli, and R. Lazzaroni, Tetrahedron: Asymmetry, 2003, 14, 1447;
6. M. Movassaghi and A. E. Ondrus, Org. Lett., 2005, 7, 4423.
7. M. Santarem, C. Vanucci-Bacqué, and G. Lhommet, J. Org. Chem., 2008, 73, 6466.
8. a) G. Jones and P. M. Radley, J. Chem. Soc., Perkin Trans.1, 1982, 1123;
9. D. Moderhack, D. Decker, and B. Holtman, J. Chem. Soc., Perkin Trans.1, 2001, 720;
10. D. Moderhack and J.-C. Schneider, J. Heterocycl. Chem., 2007, 44, 393.
11. S. Baghat, R. Sharma, and A. K. Chakraborti, J. Mol. Catal. A: Chemical, 2006, 260, 235.
12. G. Vo Thanh, J.-P. Célérier, and G. Lhommet, Tetrahedron Lett., 1999, 40, 3713.
13. In order to optimize this reaction we attempted to obtain 2a directly from 14a by treating the latter under an hydrogen atmosphere in acidic medium in order to realize the in situ deprotection of the ketone function. However, the expected product (2a) was isolated in only 22% yield, showing that a two-step procedure was preferable.
14. C. Saliou, A. Fleurant, J.-P. Célérier, and G. Lhommet, Tetrahedron Lett., 1991, 32, 3365.