1 charette/collins synthesis day may 14 2010 université de montréal, montréal, qc...
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Charette/Collins Synthesis DayMay 14 2010
Université de Montréal, Montréal, Qc
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
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 Total Synthesis of Daphnilongeranine C
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Retrosynthetic AnalysisRetrosynthetic Analysis
Main synthons prepared from readily available starting material
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Towards Malonate PartnerTowards 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 PartnerTowards 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!!!!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!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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EndgameEndgame
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