1225288-49-2Relevant academic research and scientific papers
Absolute configuration of anti-HIV-1 agent (-)-concentricolide: Total synthesis of (+)-(R)-concentricolide
Chang, Chih-Wei,Chein, Rong-Jie
experimental part, p. 4154 - 4157 (2011/06/24)
The first enantioselective total synthesis of (+)-(R)-concentricolide, the enantiomer of an anti-HIV-1 agent isolated from Daldinia concentrica, from 2-iodophenol in 7 steps reveals the (S)-configuration for the natural form of the furanophthalide. The key features include an anionic ortho-Fries rearrangement to furnish 3-iodosalicylamide, facile construction of the benzofuran system employing the tandem Sonogashira coupling annulation reaction, directed ortho metalation to introduce a propanoyl group, as well as CBS reduction, establishing the stereocenter enantioselectively.
Combined directed ortho metalation-halogen dance (HD) synthetic strategies. HD-anionic ortho fries rearrangement and double HD sequences
Miller, Ricarda E.,Rantanen, Toni,Ogilvie, Kevin A.,Groth, Ulrich,Snieckus, Victor
supporting information; experimental part, p. 2198 - 2201 (2010/08/06)
A general and efficient directed ortho metalation (DoM)-halogen dance (HD)-electrophile quench sequence for the synthesis of trisubstituted pyridyl O-carbamates is described. A second HD sequence furnishes highly functionalized tetrasubstituted pyridines.
