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Chemistry Seminar

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Carolyn Dombrowski

on 8 August 2014

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Transcript of Chemistry Seminar

Ketone Scope
Nitrone Scope: Addition by Acetophenone
Overview
Pharmaceutical Industry
Mukaiyama-Mannich Background
Prior Nitrone Work
Aim of Research
Mechanism
Ketone/Nitrone Scopes
Imine Work
Research Implications
Pharmaceutical Industry
The Mannich Reaction
Mukaiyama Aldol Reaction
Nucleophilic Addition to Nitrones
Abilify (aripiprazole)
$7.4 Billion in 2011
#6 Best Selling Drug
Crestor (rosuvastatin)
$7 Billion in 2011
# 7 Best Selling Drug
Lipitor (atorvastatin)
$13.7 Billion in 2006
#1 Best Selling Drug
Research Aim
Proposed Mechanism
Outcomes of Mannich reaction:
Ketone's alpha carbon is attached to aldehyde carbon
Aldehyde carbonyl is replaced with single bond to new nitrogen
Outcomes of the Mukaiyama Aldol Reaction:
Silyl enol ether combines with aldehyde to form 1,3 ketol under mild conditions (catalytic amounts of lewis acid required)
Imine Formation
Reaction with Imine
Research Implications and Future Work
Downey Group
Family and Friends
University of Richmond
Thanks and Questions
Aldehyde and amine combine to form imine (driven by dehydration)
Use mild conditions to induce ketone-derived enol silane reactivity to nitrones in one pot
1.
2.
Isoxazolidines
What is a Nitrone?
Nucleophilic Addition to Nitrones Cont.
3.
4.
Tomoda, Takeuchi, Nomura Chem. Lett. 1982, 1787-1790
Camiletti, Dhavale, Donati, Trombini Tetrahedron. 1995, 36, 7293-7296
Camiletti, Dhavale, Gentilucci, Trombini J. Chem. Soc., Perkin Trans. I 1993, 3157-3165
Smirnov, Sidorenkov, Khomutova, Ioffe, Tartakovsky Eur. J. Org. Chem. 2009, 3066-3074
Pharmaceutical Industry Cont.
Applications:
Pharmaceutical products:
anti-mycobacterial
anti-cancer
Industry:
anti-corrosive
Synthesis:
chiral catalysts
Pharmaceutical Industry Cont.
Johnson & Johnson.
Annual Report: Consolidated Statements of Earnings
. 2012.
Annual Report & Proxy Statements
. March 2014. 21 Jan. 2014.
From Business to Chemistry!
TMSOTf:
Amine:
Hunig's Base:
Save: time, environment, resources, cost
Changing climate for pharmaceutical providers:
Expiring patents
: generic drugs comprised about 84% of the market in 2012
Unknown long-term impact
of the Affordable Care Act
Increased demand vs. branded prescription drug fee (BPD fee)
Increasing Demand, Slowed Growth
: almost 70% of Americans use at least one prescription drug, more than 50% take two
Full transcript