simon lang problem set 1/25/13 - department of chemistry · top jacs papers of 2012 “most...
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Top JACS papers of 2012 “most downloaded over 12 months”
Simon Lang
Problem Set
1/25/13
A New Method For Direct Difluoromethylation- Phil Baran JACS 2012 1494
• No prefunctionalization- direct transfer
Mechanism?
DFMS = [Zn](SO2CF2H)2
TFA/solvent not used for mechanism Assume trace metal activates peroxide
Mechanism?
PNAS 2011 14411-14415
Rationalize these results
(+)-Scholarisine A- Amos Smith III JACS 2012 4037
20 steps from known
Provide the product
Reductive Cyclization
Rxn name?
Draw/talk through what happens?
Benzoyl Chloride DMP
Intermolecular Ritter-Type C-H Amination of Unactivated sp3 Carbons
• Phil Baran JACS 2547 2012
Inspiration
Reagent name??
Mechanism?? Think: Selectfluor = electrophillic F and Ritter rxn
R. Eric Banks, Chem Comm 1996 1629.
Nature-Inspired Total Synthesis of (-) Fusarisetin A
Emmanuel A. Theodorakis JACS 2012 5072 Nine steps from commercially available (S)-(-)-citronellal $20/g
Get here first
Via
End Game
Mechanism???