Neotripterifordin by Corey/Liu
Paul at ChemBark was writing that “the Aldrich catalog ranks #1 on my list of the top desk references of all time”. I agree, it’s a great help when looking for melting/boiling points, densities, etc. However, I have a computer 2 meters from my hood and 1 meter from my desk, so the Sigma-Aldrich website is what I mostly use.
I also have another nice desk reference. It’s the total synthesis paper of Neotripterifordin by Corey and Liu (JACS, 1997, 119, 9929-9930). Actually my desk reference is the supporting information of that paper, which is very well written and contains many common reactions.
The reactions on that paper are, for example:
LiAlH4 reduction
R-OH -> R-I
Wittig salt preparation/Wittig reaction
acetylation/deacetylation
silyl protection/deprotection
mCPBA oxidation
THP protection/deprotection
MnO2 oxidation
Katsuki-Sharpless epoxidation
benzylation
Dess-Martin oxidation
Wolff-Kishner reduction
OsO4 oxidation
Pd/C catalyzed hydrogenation
Birch reduction
[2+2] cycloaddition
ozone oxidation
DIBAL-H reduction
Barton-McCombie reaction
Oh, and this is how Neotripterifordin looks like:
There is a nice cascade reaction in that synthesis:
Interesting paper to read. I recommend.
Explore posts in the same categories: Papers
January 6, 2007 at 8:25 pm
Thanks fot the tip. That does look like a nice list of common reactions that would be handy to have reliable procedures on hand for. Cheers!
January 9, 2007 at 3:20 pm
You know, in ten years of chemistry I had never considered using a paper as a general reference resource. A nice idea and a great paper to start with. thanks.
January 30, 2007 at 2:17 am
Blogroll Update
Some may have noticed that the blogroll at left has been modernized a bit. I’ve tried to separate out the chemistry and drug industry sites – please let me know if yours has come down on the wrong side of…
February 27, 2007 at 5:45 pm
When things appear on this blog they are worth reading. HOwever, with no posts in 2 months you are officially deleted from my blog roll. Geez, people if you are going to have a blog then you should actually post!
March 9, 2007 at 9:12 am
I have a mechanism related question. What is the mechanism for the conversion of a primary alcohol to an alkyl iodide using triphenylphosphine, iodine and imidazole?
Cheers,
Sam
April 22, 2008 at 1:50 am
For procedures, I generally visit alsnotebook.com.
April 22, 2008 at 10:41 pm
Check out the supp info of Toste, Radosevich, Chan and Shih, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800554 for a impressive list of procedures..
September 23, 2008 at 6:28 pm
Iodine activates the triphenyl phosphine making iodide I- and triphenylphosphonium iodide Ph3PI+, then the alcohol reacts with the triphenylphosphonium salt to make an intermediate R-OH-P+R3, which readily deprotonated by imidazole, iodide ion displaces triphenyl phosphine oxide from the deprotonated intermediate and generates RI.
April 22, 2011 at 9:27 pm
alsnotebook.com. site will be a good help for you