Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 10, Pages 2175-2188Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403617
Keywords
Alkaloids; Nitrogen heterocycles; Lactams; Cyclization; Regioselectivity
Categories
Funding
- Council of Scientific and Industrial Research (CSIR)
- Department of Science and Technology (DST), New Delhi
- CSIR
- University Grants Commission (UGC), New Delhi
- DST-FIST
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Isoquinoline-based polycyclic lactams such as isoindoloisoquinolinones, pyrroloisoquinolinones, and benzo[a]quinolizinones were successfully assembled from the corresponding imides by using a TfOH-mediated (TfOH = trifluoromethanesulfonic acid) imide carbonyl activation and cyclization strategy. By employing this simple method, the isoquinoline alkaloids crispine A, trolline/oleracein E, and erythrinarbine were successfully synthesized in racemic form. The reaction of unsymmetrical N-phenethylphthalimides with TfOH displayed excellent regioselectivity, which was rationalized by DFT calculations.
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