88197-30-2Relevant academic research and scientific papers
A two-step biomimetic synthesis of antimalarial robustadials A and B
Bharate, Sandip B.,Singh, Inder Pal
, p. 7021 - 7024 (2007/10/03)
The antimalarial robustadials A and B have been synthesized in two steps starting from commercially available phloroglucinol comprising a key biomimetic three-component reaction that involves in situ generation of an o-quinone methide via Knoevenagel cond
The synthesis of (-)-robustadial A and some analogues
Aukrust, Inger Reidun,Skattebol, Lars
, p. 132 - 140 (2007/10/03)
The naturally occurring chroman derivative, robustadial A. and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an α,β-unsaturated acid derivative with phloroglucinol to the corresponding chromanone The isobutyl group at the 4-position was introduced with methallylzinc bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylideneacetic acid, needed for the synthesis of robustadial. was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield. Acta Chemica Scandinavica 1996.
