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Both these assignments were made using esters prepared by derivatizing the secondary OH group of the respective dipyranocoumarin. Although the assigned configurations are correct for the esters themselves, the parent secondary alcohols of these compounds should bear an opposite designation according to the Cahn-Ingold-Prelog priority rules. (See also note 15).
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7144253337
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It is important to note that an α-methoxy-α-(trifluoromethyl)-Phenylacetate derivative (MTPA ester) of an alcohol such as 2-butanol bears the same stereochemical designation (R or S) as the alcohol itself. However, with certain structures of even slightly greater complexity, such as 1-methoxy-1-butanol, the ester of the R alcohol becomes an S ester entirely as a consequence of the Cahn-Ingold-Prelog priority rules.
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0027151862
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7144250095
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note
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The data reported for calanolide C, which was originally thought to be present in C. lanigerum, was later shown to correspond to a different compound now called pseudocalanolide C (see refs 18 and 19).
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