Stereoselective Total Synthesis of (+)-Dodoneine

Abstract

A total synthesis of the naturally occurring dihydropyr­anone dodoneine is reported. The combination of a highly catalytic enantioselective allylboration and a highly diastereoselective allylstannation was used for the stereoselective generation of the two stereogenic centers. The pyranone ring was created in two steps through generation of a Z-configured α,β-unsaturated ester and lactonization via intramolecular transesterification.

Key words

asymmetric allylation - diastereoselectivity - enantio­selectivity - olefination - phenol - total synthesis - lactone

References

• 1 Ouedraogo M. Carreyre H. Vanderbrouck C. Bescond J. Raymond G. Guissou A. Cognard C. Beca F. Potreau D. Cousson A. Marrot J. Coustard J.-M. J. Nat. Prod.  2007,  70:  2006 
• 2 Àlvarez-Bercedo P. Falomir E. Carda M. Marco JA. Eur. J. Org. Chem.  2008,  4015 
• 3 Srihari P. Rajendar G. Srinivasa Rao R. Yadav JS. Tetrahedron Lett.  2008,  49:  5590 
• 4 Dittoo A. Bellosta V. Cossy J. Synlett  2008,  2459 
• 5 Rauniyar V. Hall DG. J. Org. Chem.  2009,  74:  4236 
• 6 Das B. Sunnel K. Satyalakshmi G. Nandan Kumar D. Tetrahedron: Asymmetry  2009,  20:  1536 
• 7 Sabitha G. Bhaskar V. Reddy SS. Yadav JS. Synthesis  2009,  3285. 
• 8a Allais F. Martinet S. Ducrot P.-H. Synthesis  2009,  3571 
• 8b Quentin M. Allasia V. Pegard A. Allais F. Ducrot P.-H. Favery B. Levis C. Martinet S. Masur C. Ponchet M. Roby D. Schlaich N.-L. Jouanin L. Keller H. PLoS Pathogens  2009,  5 (1): doi:10.1371/journal.ppat.1000264
• 9a Allais F. Cossy J. Org. Lett.  2006,  8:  3655 
• 9b Allais F. Louvel M.-C. Cossy J. Synlett  2007,  451 
• 9c Ferrié L. Boulard L. Pradaux F. Bouzbouz S. Reymond S. Capdevielle P. Cossy J. J. Org. Chem.  2008,  73:  1864 
• 9d Ferrié L. Reymond S. Capdevielle P. Cossy J. Org. Lett.  2007,  9:  2461 
• 10 Still WC. Gennari C. Tetrahedron Lett.  1983,  24:  4405 
• 11a Rychnovsky SD. Rogers BN. Richardson TI. Acc. Chem. Res.  1998,  31:  9 
• 11b Rychnovsky SD. Rogers BN. Guang YO. J. Org. Chem.  1993,  58:  3511 
• 12 McNeill AH. Thomas EJ. Synthesis  1994,  322 
• 13 Keck GE. Byers JH. J. Org. Chem.  1985,  50:  5442