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

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Whakataku
#1
May3-12, 02:58 PM
P: 12
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?
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Whakataku
#2
May3-12, 03:04 PM
P: 12
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??
Whakataku
#3
May4-12, 12:42 PM
P: 12
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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