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Koreeda M, Brown L, Vald. 
“The Absolute Stereochemistry of Salvinorins”. 
The Chemical Society of Japan. 1990 Aug 06;19(11):2015-8.
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 lU 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 stereochemistry 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 negative n → π* Cotton effect of isofructicolone,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)
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