ERRORS IN THE NDPSC’S SYSTEMATIC NAME FOR SALVINORIN A

Let's compare the name endorsed by the NDPSC’s “technical experts” with the one used by Chemical Abstracts Service, one of the world's highest authorities on chemical nomenclature.

Technical Experts:

"8-METHOXYCARBONYL-4A,8A-DIMETHYL-6-ACETOXY- 5-KETO-3,4,4B,7,9,10,10A-SEPTAHYDRO-3-(4-FURANYL)- 2,1-NAPHTHO[4,3-E]PYRONE"

Chemical  Abstracts Service:

"(2S,4aR,6aR,7R,9S,10aS,10bR)- 9-(acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl- 4,10-dioxo-2H-Naphtho[2,1-c]pyran-7-carboxylic acid, methyl ester"

Note the following errors in the NDPSC name:

• Every number is incorrect.
• The stereochemistry, an essential feature, is unspecified and therefore ambiguous.
• The term “septa” is meaningless (and the actual term for seven, “hepta”, is incorrect here anyway).
• The locants "2,1-" preceding the parent compound are meaningless.

Apart from these major errors, there are less serious deviations from IUPAC recommendations such as the non-alphabetical ordering of the prefixes, the selection of the ketone rather than the ester as suffix, and the use of “keto” rather than “oxo”.

(For more information, see IUPAC’s guidelines, and their update on fused-ring systems like salvinorin A)

You may be wondering: how is it possible to get the name so wrong? The real author, William E. White, explains his confusion:

"I tried to get an IUPAC name out of this; unfortunately, I gagged when  trying to decide whether it was a naphthopyrone, or a modified  phenanthrene, or whether it should start from cyclohexane instead of  aromatic rings, or whatever. The fact that phenanthrene is numbered  funny didn't help ... Sorry, I haven't done o-chem since the Reagan administration."[1]

So he compromised; he named it one way, and numbered it another. No wonder it's "numbered  funny"!

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