Organic Chemistry Nomenclature Question

Jul 2013
1
1
I'm writing up some work on opioids and am trying to decide how to name them. Having spent a while slogging my way through the IUPAC rules I've come up with a few different ways, all are semisystematic in that they incorporate either the parent 'morphinan' or 'oripavine'. I'd really like some feedback, comments, objections, suggestions, etc. from other chemists as to what they think.

All comments very welcome; you don't need to go through checking all of the stereochem (though please do if you'd like!). Examiner quite big on conformity to conventions, which is no bad thing necessarily, so the closer to IUPAC perfection, the better!

As my compounds are similar in structure to buprenorphine (http://opioids.com/buprenorphine/buprenorphine.jpg) I'll show the four different ways for that compound:

Format 1 (morphinan as substituent on butan-2-ol):
(2S)-2-[(5R,6R,7R,14S)-17-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

Format 2 (all the substituents coming off morphinan-3-ol:
(5R,6R,7R,9R,13R,14S)-17-Cyclopropylmethyl-7-[(S)-3,3-dimethyl-2-hydroxybutan-2-yl-]-4,5-epoxy-6,14-ethano-6-methoxymorphinan-3-ol

Format 3 (all the substituents coming off morphinan)
(5R,6R,7R,9R,13R,14S)-17-Cyclopropylmethyl-7-[(S)-3,3-dimethyl-2-hydroxybutan-2-yl-]-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan

Format 4 (all substituents coming off oripavine and stereochemistry described both in absolute terms (R/S) and with reference to projection above or below the plane of the molecule (beta/alpha))
21-Cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
 
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Unknown008

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I'm not really a chemist, but kudos on the attempt to name such a compound, I don't think I'd ever have the patience to name something like that! :p

This said, I can't really give you feedback on the namings you came up with, but I know this site where the main different synonyms synonyms of compounds can be found and your last format is the same as one of those! I hope it can help you coming up with better names some way or another :)

Otherwise, wishing you the best.