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Synthesis of carbazole analogs via Grob fragmentation of norbornyl α-diketones.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Aug2016, Vol. 57 Issue 31, p3449-3452. 4p. - Publication Year :
- 2016
-
Abstract
- A regioselective synthesis of carbazole analogs belonging to both the categories of natural origin, viz., microorganisms and higher plant source is reported. The synthesis of carbazole derivatives possessing a methylester group at C-1 position has been achieved by Cadogan cyclization of nitro bi-phenyl derivatives, whereas, the carbazole analog possessing a methylester group at C-3 position was synthesized by Buchwald–Hartwig Pd-catalyzed cyclization of amino bi-phenyl derivatives. Suitably substituted bi-phenyl precursors were accessed from norbornyl α-diketones via Grob fragmentation, O-methylation and DBU aromatization reaction sequence. The reported carbazole derivatives possess structural features that are common with many carbazole natural products: mukonine, clausine-L, murrayafoline-A, and their sibling natural products. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 57
- Issue :
- 31
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 116760400
- Full Text :
- https://doi.org/10.1016/j.tetlet.2016.06.080