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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 [email protected]. Charette/Collins Synthesis Day May 14 2010 - PowerPoint PPT Presentation
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Charette/Collins Synthesis DayMay 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
Total Synthesis of Daphnilongeranine C
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Retrosynthetic Analysis
Main synthons prepared from readily available starting material
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Towards Malonate Partner
J. Org. Chem. 1980, 45, 4129
J. Am. Chem. Soc. 1998, 120, 3903
Org. Lett. 2009, 11, 4358
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Towards Malonate Partner
J. Am. Chem. Soc. 2007, 129, 10356J. Am. Chem. Soc. 1984, 106, 1079
Tetrahedron Lett. 1995, 36, 2531
10 Steps to First Synthon
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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, 5746Org. Lett. 2005, 7, 5461
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Forward and Onward!
J. Org. Chem. 2003, 62, 5746Org. Lett. 2005, 7, 5461
Tetrahedron 2005, 61, 4053
WO2009/49112 A1 2009
PHILIPP, ARE YOU AWAKE???
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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%
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Thank you iNMR for nicer looking spectra