70779-43-0Relevant academic research and scientific papers
Catalytic Asymmetric Total Syntheses of Naturally Occurring Amarylidaceae Alkaloids, (-)-Crinine, (-)- epi-Crinine, (-)-Oxocrinine, (+)- epi-Elwesine, (+)-Vittatine, and (+)- epi-Vittatine
Das, Mrinal K.,Kumar, Nivesh,Bisai, Alakesh
, p. 4421 - 4424 (2018)
An expeditious approach to catalytic enantioselective total syntheses of crinine-type Amaryllidaceae alkaloids has been accomplished via a Pd-catalyzed enantioselective decarboxylative allylation of allylenol carbonates as a key step (up to 96% ee). Using this strategy, collective total syntheses of Amaryllidaceae alkaloids such as (-)-epi-elwesine (1b), (-)-crinine (1c), (-)-epi-crinine (1e), (-)-oxocrinine (1f), and (-)-buphanisine (1d) have been accomplished. Gratifyingly, naturally occurring Amaryllidaceae alkaloids such as (+)-vittatine (1g), (+)-epi-vittatine (1h), and (+)-epi-elwesine (1i) [enantiomers of (-)-1c, (-)-1e, and (-)-1b, respectively] have also been achieved by switching the antipode of ligand used in the catalytic enantioselective step.
Total syntheses of (+)- and (?)-Crinane via Pd(0)-Catalyzed deacylative allylation
Das, Mrinal K.,Yadav, Abhinay,Majumder, Satyajit,Mondal, Ayan,Bisai, Alakesh
supporting information, (2021/02/09)
An efficient Pd(0)-catalyzed deacylative allylation (DaA) of enolcarbonates (pro-nucleophile) prepared from 2-arylcyclohexanones sharing acyl functionality at C2-position with readily available allylic alcohols (pro-electrophiles) by employing Pd(0)-catalysis under mild reaction conditions. The methodology can be extended for deacylative benzylations (DaB) of enolcarbonates of 2-arylcyclohexanones. As an application of our methodology, we have shown asymmetric total synthesis of Amaryllidaceae alkaloids, (+)- and (?)-crinane.
Catalytic deacylative alkylations (DaA) of enolcarbonates: Total synthesis of (±)-Crinane
Das, Mrinal K.,Yadav, Abhinay,Majumder, Satyajit,Bisai, Alakesh
supporting information, (2020/07/03)
An efficient Pd(0)-catalyzed deacylative allylation (DaA) of enolcarbonates (as pro-nucleophile) of cycloalkanones sharing acyl functionality at C2-position with readily available allylic alcohols (as pro-electrophiles) is disclosed under mild reaction conditions. A wide variety of cycloalkanones with an aromatic ring and allyl group at C-2 position (all-carbon quaternary center) are obtained in good to excellent yields (36 examples). The usefulness of this methodology has been shown by a total synthesis of Amaryllidaceae alkaloid, (±)-crinane from 2-aryl cyclohexanone in 5 steps.
Synthesis of Sceletium and Amaryllidaceae Alkaloids, (+/-)-Mesembrine and (+/-)-Dihydromaritidine, (+/-)-Epidihydromaritidine, (+/-)-Elwesine, and (+/-)-Epielwesine
Hoshino, Osamu,Sawaki, Shohei,Shimamura, Naomi,Onodera, Akira,Umezawa, Bunsuke
, p. 2734 - 2743 (2007/10/02)
The alkylation of 2-arylcyclohexanones (12b and 6) with alkyl halides or acrylonitrile and 50percent aq. sodium hydroxide in the presence of a phase-transfer catalyst (18-crown-6) was found to give readily 2-alkyl-2-arylcyclohexanones (14 and 16) in fair
