Studies directed toward total synthesis of rhodocomatulins: A regioselective synthesis of brominated hydroxyanthraquinones by anionic annulations |
| |
Authors: | Md Raja Sk Soumen Chakraborty |
| |
Institution: | Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India |
| |
Abstract: | In this work, brominated hydroxyanthraquinones, which are the core structural motif of naturally occurring bromorhodocomatulins, were successfully synthesized using Hauser annulation reaction as the key step. When brominated Michael acceptors (brominated p-quinone monoketals) and cyanophthalides or bromocyanophthalides (Hauser donors) were reacted under the annulation conditions, brominated anthraquinones were obtained with 81–87% yields for four examples. On acidic quenching, products were obtained as solid which were separated by filtration and purified by recrystallization in acetone. No chromatography was required. |
| |
Keywords: | Brominated hydroxyanthraquinones Hauser annulation rhodocomatulins |
|
|