1. 1 Charette/Collins Synthesis Day May 14 2010 Université de Montréal, Montréal, Qc Charette/Collins Synthesis Day May 14 2010 Université de Montréal, Montréal, Qc 7th Heaven (plus Scott), and André B. Charette* Département de chimie, Université de Montréal, C.P. 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7 andre.charette@umontreal.ca 7th Heaven (plus Scott), and André B. Charette* Département de chimie, Université de Montréal, C.P. 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7 andre.charette@umontreal.ca Total Synthesis of Daphnilongeranine C

2. 2 Retrosynthetic Analysis Main synthons prepared from readily available starting material

3. 3 Towards Malonate Partner J. Org. Chem. 1980, 45, 4129 J. Am. Chem. Soc. 1998, 120, 3903 Org. Lett. 2009, 11, 4358

4. 4 Towards Malonate Partner J. Am. Chem. Soc. 2007, 129, 10356 J. Am. Chem. Soc. 1984, 106, 1079 Tetrahedron Lett. 1995, 36, 2531 10 Steps to First Synthon

5. 5 Longest Linear Starts..... NOW!!!! Tetrahedron Lett. 1999, 40, 2699 Tetrahedron 1985, 41, 375 J. Am. Chem. Soc. 2007, 129, 9086 J. Org. Chem. 2003, 62, 5746 Org. Lett. 2005, 7, 5461

6. 6 Forward and Onward! J. Org. Chem. 2003, 62, 5746 Org. Lett. 2005, 7, 5461 Tetrahedron 2005, 61, 4053 WO2009/49112 A1 2009 PHILIPP, ARE YOU AWAKE???

7. 7 Endgame Tsuji, J. Palladium Reagents and Catalysis. 2004, Wiley. Tetrahedron Lett. 1983, 24 3841. J. Am. Chem. Soc. 2007, 129, 10356 16 LONGEST LINEAR SEQUENCE !!!!!! 27 steps total 8.31 G of Product Overall yield of 83.45286%

8. 8 Thank you iNMR for nicer looking spectra