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

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 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