Abstract
Both enantiomers of 3α,6β-dibenzoyloxytropane (1) have been prepared from optical active 6β-hydroxyhyoscyamines establishing their absolute configurations as (−)-(3R,6R) and (+)-(3S,6S)-dibenzoyloxytropane. Independent stereochemical confirmation was obtained by vibrational circular dichroism measurements, since bands characteristic of (3R,6R) and (3S,6S) configurations of tropanediols derivatives were observed. In addition, a chiral HPLC method was developed for determining absolute configurations of tropane-related natural substances at the microgram (μg) level. The complete 1H NMR characterization of the scaffold of 1 is also reported.
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