Confirmation of the NMR assignments of salvinorin A

Thomas A. Munro,
Mailman Research Center, McLean Hospital, 115 Mill St, Belmont MA 02478, USA
Phone: +1 617 855 2095
Fax: +1 617 855 3479
tmunro@mclean.harvard.edu

The editor, Magnetic Resonance In Chemistry:

Giner and coworkers provide valuable new 1H NMR data for salvinorin A.1 In
particular, they provide the first accurate estimates of the coupling constants for several
non-first order multiplets, giving new information about the conformation of salvinorin A
in solution. However, the belief that their assignments differ from those in an earlier
publication2 stems from a misinterpretation. Configuration (α vs β) was not assigned in
that work. Diastereotopic methylene signals were labelled “a” and “b” in order of
appearance (as recommended, for instance, by the Journal of Natural Products). The
assignments given in that work,2 while incomplete, are consistent with the complete
assignments reported subsequently.3 Given that those complete assignments have now
been independently confirmed by Giner and coworkers, they can be considered firmly
established. This is also true of the original 13C NMR assignments by Valdés and
coworkers,4 which have now been independently verified twice.
Yours sincerely,
Thomas Munro
1. Giner JL, Kiemle DJ, Kutrzeba L, Zjawiony J. Magn. Reson. Chem. 2007; 45: 351.
doi: 10.1002/mrc.1972
2. Munro TA, Rizzacasa MA, Roth BL, Toth BA, Yan F. J. Med. Chem. 2005; 48: 345.
doi: 10.1021/jm049438q
3. Munro TA. The Chemistry of Salvia divinorum. PhD Thesis, University of Melbourne,
2006. [http://eprints.infodiv.unimelb.edu.au/archive/00002327]
4. Valdés LJJ, III, Butler WM, Hatfield GM, Paul AG, Koreeda M. J. Org. Chem. 1984;
49: 4716. doi: 10.1021/jo00198a026

This is a preprint of an article published as:

Munro, T. A., Confirmation of the NMR assignments of salvinorin A.
Magn. Reson. Chem. 2007, 45, 801. doi: 10.1002/mrc.2020

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