Organic Chem Nomenclature Question

[halcyonmind]

Hello,

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 closer to the 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