Controlled epimerization of indolo[2,3-a]quinolizidine derivatives: An efficient total synthesis of (±)-tacamonine
✍ Scribed by Mauri Lounasmaa; Kimmo Karinen; David Din Belle; Arto Tolvanen
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 542 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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Acid-eatalysed epimerization of 1-, 2-and 3-monosubstituted 1,2,3,4,6,7,12,12boctahydroindolo[2,3-a]quinolizine alkyl derivatives in refluxing trifluoroacetic acid (TFA) leads to an equilibrium mixture of C-12b diastereomers. The thermodynamically more stable epimer predominates over the kinetically
The role of the nitrogen lone pairs in the mechanism of the acid-catalysed epimerization of indolo[2,3-a]quinolizidines is investigated using laetams as model compounds. Deethylebumamonine (3) did not epimerize with trifluoroacetic acid (TFA), whereas deethyldihydroeburnamenine (7) underwent epimeri
Efficient, stereocontrolled total synthesis of the title compound is described, starting from enantiopure intermediates. A key step was the diastereoselective catalytic hydrogenation of a pentacyclic oxazepinohexahydroindolo[2,3-a]quinolizine derivative.