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IUPAC dilemma on naming a toxin, any pro organic chemists out there?

  1. May 3, 2012 #1
    So I came across a cool toxin, and saw that people have not assigned an IUPAC name to it, so I took on the challenge.

    The compound of interest is Batrachotoxinin A

    unc.
    edu/depts/mtcgroup/litmeetings/batrachotoxinin.pdf

    In the second slide Batrachotoxinin A has an R which is an H instead of a pyrolle moiety.

    Now Batrachotoxinin A's relative Batrachotoxin (the one with the pyrolle moiety) has the following IUPAC name

    1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, (1S)-1-[(5aR, 7aR, 9R, 11aS, 11bS, 12R, 13aR)-1,2,3,4,7a,8,9,10,11,11a , 12,13- dodecahydro-9,12-dihydroxy-2, 11a-dimethyl- 7H-9,11b-epoxy-13a, 5a-propenophenanthro[2,1-f] [1,4] oxazepin-14-yl] ethyl ester


    So is the Batrachotoxinin A's IUPAC
    (1S)-1-[(5aR, 7aR, 9R, 11aS, 11bS, 12R, 13aR)-1,2,3,4,7a,8,9,10,11,11a , 12,13- dodecahydro-9,12-dihydroxy-2, 11a-dimethyl- 7H-9,11b-epoxy-13a, 5a-propenophenanthro[2,1-f] [1,4] oxazepin-14-yl] ethyl ester

    (As you can see I just deleted 1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-,)

    is that ok?
     
  2. jcsd
  3. May 3, 2012 #2
    Wait I take that Batrachotoxinin A does not have carboxylic acid any more, but a hydroxy group, so it's not an ester, but an alcohol.

    So I somehow have to name it with a substituted ethanol??

    Any hints??
     
  4. May 4, 2012 #3
    Never mind, I found the name:

    [5[itex]\alpha[/itex]R-[5[itex]\alpha[/itex][itex]\alpha[/itex],7[itex]\alpha[/itex][itex]\beta[/itex],9[itex]\alpha[/itex],11[itex]\alpha[/itex][itex]\beta[/itex],11[itex]\beta[/itex][itex]\alpha[/itex],12[itex]\alpha[/itex],13[itex]\alpha[/itex][itex]\alpha[/itex],14(S*)]]-1,2,3,4,7a,10,11,11[itex]\alpha[/itex],12,13-Decahydro-14-(1-hydroxyethyl)-2,11[itex]\alpha[/itex]-dimethyl-7H-9,11[itex]\beta[/itex]-epoxy-13[itex]\alpha[/itex],5[itex]\alpha[/itex]-propenophenanthro[2,1-f][1,4]oxazepine-9,12(8H)-diol
     
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