Acta Crystallographica Section E

Structure Reports Online

Volume 68, Part 11 (November 2012)

organic compounds

qm2086 scheme

Acta Cryst. (2012). E68, o3225-o3226    [ doi:10.1107/S1600536812043449 ]

Salvinorin B methoxymethyl ether

T. A. Munro, D. M. Ho and B. M. Cohen

Abstract: The title compound [MOM-SalB; systematic name: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(3-furyl)-9-methoxymethoxy-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate], C23H30O8, is a derivative of the [kappa]-opioid salvinorin A with enhanced potency, selectivity, and duration of action. Superimposition of their crystal structures reveals, surprisingly, that the terminal C and O atoms of the MOM group overlap with the corresponding atoms in salvinorin A, which are separated by an additional bond. This counter-intuitive isosterism is possible because the MOM ether adopts the `classic anomeric' conformation (gauche-gauche), tracing a helix around the planar acetate of salvinorin A. This overlap is not seen in the recently reported structure of the tetrahydropyranyl ether, which is less potent. The classic anomeric conformation is strongly favoured in alkoxymethyl ethers, but not in substituted acetals, which may contribute to their reduced potency. This structure may prove useful in evaluating models of the activated [kappa]-opioid receptor.

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