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:

Neotripterifordin

There is a nice cascade reaction in that synthesis:

Neotripterifordin cascade reaction

Interesting paper to read. I recommend.

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10 Comments on “Neotripterifordin by Corey/Liu”

  1. Russ Says:

    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!

  2. agogmagog Says:

    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.


  3. 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…

  4. Wondering Says:

    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!

  5. Samantha Wimala Says:

    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

  6. pmgb Says:

    For procedures, I generally visit alsnotebook.com.

  7. pmgb Says:

    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..

  8. gra Says:

    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.

  9. neo Says:

    alsnotebook.com. site will be a good help for you


  10. hmm…Chemistry is inbriety for me Witting Salt especially ,<3 it.


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