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Mitorubrin   

24 October 2006 4,508 views 6 Comments

mitorubin.jpg

Porco and Zhu. Org. Lett., 2006, ASAP. DOI: 10.1021/ol062233m.

This concise synthesis of various members of the Mitorubin family by John Porco might be less controversial than my last post on his work, but it’s no less impressive. The centerpiece (for me at least) is a pair of copper-mediated transformations, appending the second ring and completing the core structure:

mitorubin_1.jpg

In the first reaction, the Cu(III)-spartine complex is used stoichiometrically, but to my eye doesn’t look too expensive… the methodology is discussed in this JACS from last year. The crude product from this reaction was then submitted to a Cu(I) catalysed cycloisomerisation, and acheived a 58% yield over the pair of steps – none too shoddy considering the complexity of the transformation.

BTW, props to Dr. Luke for pointing this one out to me…

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6 Comments

  • Prelim Passed says:

    Anyone see the retraction from ACIEE by Porco in the last week? Probably an honest mistake, but still, it seems like something the refs should have questioned. I’m losing most of my respect for that journal.

  • anon says:

    Good catch. Without that reaction, the reason for the original paper is more or less negated, regardless of whether the lead up chemistry is valid. A very diplomatic, very subtle retraction.
    http://www3.interscience.wiley.com/cgi-bin/abstract/113390896/ABSTRACT

  • yepyep says:

    Some nice chemistry in this one.

    About the retracted (was it really retracted?) paper: I find it quite weird that they assigned the structure incorrectly in the original paper. IR shows peaks at 1727, 1672 and 1652 and 13C NMR 187.1, 185.5 and 172.4 which both scream to me “3 carbonyls!”.

  • regular chem says:

    About the retracted (was it really retracted?) paper, I personally think it is the resposibility of the professor himself to make sure the structure is correct, not the referees’. The reviewers tend to give the authors the benefit of doubt. It is sad to see that this kind of mistakes happen. However it reflects the ineffecient training of the professor himself. In a rigourouly-trained group, each new or known compound has to match a structure-identification form consisting of proton carbon NMr, MS, IR,etc. thus eliminating such easy mistakes. I have known that some professors just take whatever results their students produce without ever questioning their authenticity.
    It is understandable for people to make small mistakes. However the boss should have checked the correctness of the structure himself, i.e., examining the NMR data as well as other informations first hand consirdering the importantance of the structure which was the center piece of the paper. It is even funny to see that they put up a ton of similated and similar compounds’ data at the end of the supplementary information in order to validate their claimed compound.You can call it an honest mistake, but being ignorant maynot be qualified as being honest.

  • ddd says:

    yay….Porco goes down :)))

  • European Chemist says:

    100% agree with you, regular chem. We all know that group leaders have other stuff to do than checking their students’ spectral data, that’s clear. But in key transformations that are to be published, I don’t take it as offensive or abusive if the Boss asks to see the data collected in support of the structures I present to him on the blackboard – in the end, it’s HIS “bottom” that’s on the line if things prove to be different from what I thought. It’s HIS name that gets the little star at the end of the paper because HE takes responsibility for the work presented.

    It’s been “retraction season” in top-notch journals or what?? :-D