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Charette/Collins Synthesis Day May 14 2010 Université de Montréal, Montréal, Qc

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

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Charette/Collins Synthesis Day May 14 2010 Université de Montréal, Montréal, Qc

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  1. Total Synthesis of Daphnilongeranine C 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 Charette/Collins Synthesis Day May 14 2010 Université de Montréal, Montréal, Qc

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

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

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

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

  6. Forward and Onward! J. Org. Chem. 2003, 62, 5746 Org. Lett. 2005, 7, 5461 Tetrahedron 2005, 61, 4053 PHILIPP, ARE YOU AWAKE??? WO2009/49112 A12009

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

  8. Thank you iNMR for nicer looking spectra

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