1397496-03-5Relevant academic research and scientific papers
Total synthesis of (±)-powelline and (±)-buphanidrine
Bogle, Katherine M.,Hirst, David J.,Dixon, Darren J.
, p. 1252 - 1254 (2010)
Chemical Equation Presented The total synthesis of (±)-powelline (13 linear steps in an overall yield of 6%) and (±)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.
Oxidative cross-coupling reaction of catechols with active methylene compounds in an aqueous medium using an AlPO4-supported Ru catalyst
Maeno, Zen,Yamamoto, Masanobu,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro
, p. 5401 - 5405 (2018/11/20)
A green oxidative coupling reaction of catechols with active methylene compounds was achieved using an AlPO4-supported Ru catalyst, where O2 and H2O were used as the ideal oxidant and solvent, respectively. The catalyst is
Laccase-catalysed α-arylation of cyclic β-dicarbonyl compounds
Pietruszka, Joerg,Wang, Chuan
, p. 2402 - 2409 (2013/02/21)
In this protocol we described an environmentally friendly synthesis of α-arylated cyclic β-dicarbonyl compounds employing various catechols as precursors through an oxidation/Michael addition sequence. The process proceeded under the catalysis of a commercially available laccase at room temperature with the use of aerial oxygen as the oxidant affording the products in moderate to excellent yields (36-96%). Furthermore, a highly functionalized cyclopentane bearing an all-carbon quaternary stereogenic centre was synthesized through the arylation in excellent diastereoselectivity (dr > 99 : 1, 95% ee).
An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine
Bogle, Katherine M.,Hirst, David J.,Dixon, Darren J.
experimental part, p. 6399 - 6410 (2010/10/19)
Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleop
