chem 430 – structural analysis of organic compounds spring 2014
TRANSCRIPT
IntroductionOur approach must differ depending on the type of work we are performing.
1. “Cold” analysis – the unknown organic is a complete unknown• Forensic chemistry• EPA methods and related analyses• Natural products taxonomy
In these cases, little if anything is known about the individual compounds – detective work must recreate the entire structure
2. Results of a synthetic experiment
In this case, the majority of the structure should be maintained, the goal is to analyze for and confirm changes
3. Characterization for the chemical literature – Assignments!
The analysis here is to confirm the author’s findings and serve as a benchmark for further work on the compound
Limitations (and grades)We can only see what our ‘shutter speed’ allows:
Technique Timescale
X-ray diffraction 10-18
UV 10-15
Visible 10-14
IR 10-13
ESR 10-4 to -8
NMR 10-1 to -9
Mössbauer 10-7
Experimental separation of isomers
102
Limitations (and grades)Can we ever achieve a fully secure structure (or why did I get it wrong?)?
Harrisonin
Heterocycles 1976, 5, 485.
J. Nat. Prod. 1997, 60, 822
Limitations (and grades)Can we ever achieve a fully secure structure (or why did I get it wrong?)?
J. Am. Chem. Soc. 1983, 105, 6312.
Tetrahedron Lett. 1992, 33, 3711J. Antibiotics 1986, 39, 1527
Limitations (and grades)Can we ever achieve a fully secure structure (or why did I get it wrong?)?
J. Org. Chem. 2001, 66, 8717.
Tetrahedron Lett. 2003, 44, 1203
Limitations (and grades)Can we ever achieve a fully secure structure (or why did I get it wrong?)?
J. Nat. Prod. 2000, 63, 1677.
J. Nat. Prod. 2003, 66, 716
Limitations (and grades)Can we ever achieve a fully secure structure (or why did I get it wrong?)?
J. Am. Chem. Soc. 2003, 125, 5296.Org. Lett. 2004, 6, 2607
Spirastrellolide
Limitations (and grades)Can we ever achieve a fully secure structure (or why did I get it wrong?)?
J. Nat. Prod. 2007, 70, 412.
J. Am. Chem. Soc. 2008, 130, 804
(+)-Neopeltolide