Synthesis of the 3,4,5-Trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl) benzaldehyde for Divergent Preparation of Cytotoxic Biaryls

Title:Synthesis of the 3,4,5-Trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl) benzaldehyde for Divergent Preparation of Cytotoxic Biaryls

Volume: 9 Issue: 8

Author(s): Raphael Labruere, Philippe Helissey, Stephanie Desbene-Finck and Sylviane Giorgi-Renault

Affiliation:

Keywords: Carbaldehydes, cytotoxic biaryls, lignans, phenanthridines, regioselective nitration, stille coupling, biphenyl, antitumor drugs, steganone, eupomatilone-6.

Abstract: The regioselective synthesis of the 3,4,5-trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl)benzaldehyde as key intermediate for divergent preparation of cytotoxic biaryl lignans was achieved in three steps from commercially available starting materials. Reactivity of this synthon was illustrated by its conversion into the corresponding phenanthridine and bromomethylbenzene.

Cite this article as:

Labruere Raphael, Helissey Philippe, Desbene-Finck Stephanie and Giorgi-Renault Sylviane, Synthesis of the 3,4,5-Trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl) benzaldehyde for Divergent Preparation of Cytotoxic Biaryls, Letters in Organic Chemistry 2012; 9 (8) . https://dx.doi.org/10.2174/157017812802850276