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Bistramide A   

29 March 2006 6,166 views 5 Comments

bistramide.jpg
Crimmins and DeBaillie. JACS, 2006, ASAP. DOI: 10.1021/ja057686l

All in the name, this one. Obviously a bisamide, so even the undergrads would get the major disconnections in this one! They put the spiroketal in very nicely though, alkylating and hydrogenating to give the desired product in 83% over two steps.

bistramide_2.jpg

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5 Comments

  • anonym says:

    although it looks quite simple, biological activity is impressive though. Nice work was done to identify its mechanism of action. Some other syntheses are impressive also :)

  • NoName says:

    alkyne proton is missing, i guess.

  • Tot. Syn. says:

    Damn! You got me – however, the wonders of photoshop never cease! That Add-A-Proton-To-An-Acetylene function is ace.

  • NoName says:

    I seriously doubt how this work got to JACS. Comparing to Kozmin’s work (published in JACS 2004), it has more steps, lower total yield. More ironically, it basically copied the end-game reactions, even the protecting groups! Also, it still said the target was PKC in the introduction, while the mode of action studies were already published!

  • NoName says:

    “the mode of action studies were already published”
    Decemeber 2005 in NatChemBiol, this one is published in April 2006.
    I think you’re “technically” right, NoName :)