Synthesis of Carbazole Analogs via Grob Fragmentation of Norbornyl α-Diketones

Kadavergu, S and Agrawal, S K and Chintada, N R and Khan, Faiz Ahmed (2016) Synthesis of Carbazole Analogs via Grob Fragmentation of Norbornyl α-Diketones. Tetrahedron Letters, 57 (31). pp. 3449-3452. ISSN 0040-4039

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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 posses structural features that are common with many carbazole natural products: Mukonine, Clausine-L, Murrayafoline-A and their sibling natural products.

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