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Salvia divinorum photos from L. J. Valdes III http://www.sagewisdom.org/valdesphotos.html (2 of 2) [04.09.01 10:21:57]
(stereochem.) The Absolute Stereochemistry of Salvinorins Masato KOREEDA,* Lindsey BROWN, and Leander J. VALDÉS III Department of Chemistry, The University of Michigan, Ann Arbor Michigan 48109, U.S.A. HTML by Arachnophilia Chemistry Letters, pp. 2015-2018, 1990. The absolute stereostructures of the hallucinogenic diterpenes Salvinorin A and B have been unambiguously determined by the use of the non-empirical exciton chirality circular dichroism method on their 1α,2α-diol dibenzoate derivative. Recent investigations1,2) of the hallucinogenic Mexican mint Salvia divinorum3) have resulted in the isolation of the pharmacologically active diterpene salvinorin (divinorin) A (1) and its desacetyl analog salvinorin B (2). Extensive 1H and 13C NMR studies on these trans-clerodanes1,2) and their derivatives, 2) as well as single-crystal X-ray analysis,1,2) have led to the formulation of the structures of these compounds. The absolute chemistry of the salvinorins was postulated based on the observed negative n→π* Cotton effect of the 1-ketone around 295 nm in their circular dichroism (CD) spectra. 1,2) While this assignment had appeared to be corroborated by the n→π* Cotton effect of isofruticolone, 4) the ambiguous nature of the approach associated with this empirical CD method necessitated an independent, unequivocal verification of the absolute stereochemistry. In the following, we delineate the unambiguous assignment of the absolute stereochemistry of these physiologically important diterpenes through the use of the non-empirical exciton chirality CD method. 5) http://www.sagewisdom.org/stereochemistry.html (1 of 5) [04.09.01 10:21:59]
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type_Document_Title_here Salvinorin
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Page 377 and 378: DivinorinJOC1984 Figure 1. Divinori
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