54314-84-0Relevant articles and documents
Synthesis of the Core Structure of Palhinine A
Gaugele, Dominik,Maier, Martin E.
, p. 2549 - 2556 (2021/06/28)
We present a strategy to the core structure of the alkaloid palhinine A passing through a 2,5-difunctionalized cyclohexenone. This enone was prepared by a domino Michael/aldol condensation sequence. An allylation reaction on the cyclohexenone followed by
Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes
Jones, Caleb A. H.,Schley, Nathan D.
supporting information, p. 1744 - 1748 (2019/02/20)
Catalysts capable of heterolytic silane activation have been successfully applied to the conversion of alkyl ethers to silyl ethers via C-O bond cleavage. The previously-reported cationic pincer-supported iridium complex for this transformation suffers fr
Photocatalyic Appel reaction enabled by copper-based complexes in continuous flow
Minozzi, Clémentine,Grenier-Petel, Jean-Christophe,Parisien-Collette, Shawn,Collins, Shawn K.
supporting information, p. 2730 - 2736 (2018/11/21)
A copper-based photocatalyst, Cu(tmp)(BINAP)BF4, was found to be active in a photoredox Appel-type conversion of alcohols to bromides. The catalyst was identified from a screening of 50 complexes and promoted the transformation of primary and secondary alcohols to their corresponding bromides and carboxylic acids to their anhydrides. The protocol was also amendable and optimized under continuous flow conditions.
A concise stereoselective synthesis of (+)-1-deoxy-6-epi-castanospermine
Gajare, Vikas S.,Khobare, Sandip R.,Datrika, Rajender,Reddy, K. Srinivasa,Rajana, Nagaraju,Babu, B. Kishore,Rao, B. Venkateswara,Syam Kumar
supporting information, p. 1486 - 1488 (2016/03/12)
A concise stereoselective synthesis of (+)-1-deoxy-6-epi-castanospermine has been developed through stereoselective approach from the chiral precursor R-Glycidol. The key steps in the synthesis involve Grignard reaction through Weinreb amide, followed by Sharpless dihydroxylation and stereoselective reduction of imine assigned the required stereochemical feature of indolizidine azasugar (+)-1-deoxy-6-epi-castanospermine.
Light-mediated deoxygenation of alcohols with a dimeric gold catalyst
McCallum, Terry,Slavko, Ekaterina,Morin, Mathieu,Barriault, Louis
supporting information, p. 81 - 85 (2015/02/18)
A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.
Synthetic studies on lycopodine: Construction of hexahydrojulolidine core by intramolecular Mannich reaction
Sato, Takanao,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 7177 - 7180 (2015/01/09)
The tricyclic core skeleton of lycopodine was constructed by the intramolecular Mannich reaction of a 12-membered cyclic amine. The concise assembly of the macrocyclic intermediate was executed by the sequential inter- and intramolecular N-alkylation of a
Syntheses of the Stemona alkaloids (±)-stenine, (±)- neostenine, and (±)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction
Frankowski, Kevin J.,Golden, Jennifer E.,Zeng, Yibin,Lei, Yao,Aube, Jeffrey
, p. 6018 - 6024 (2008/09/20)
A tandem Diels-Alder/azido-Schmidt reaction sequence provides rapid access to the core skeleton shared by several Stemona alkaloids including stenine, neostenine, tuberostemonine, and neotuberostemonine. The discovery and evolution of inter- and intramole
BORON-CONTAINING SMALL MOLECULES
-
Page/Page column 220, (2009/01/23)
This invention provides, among other things, novel compounds useful for treating bacterial infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.
A combined intramolecular Diels-Alder/intramolecular Schmidt reaction: Formal synthesis of (±)-stenine
Golden, Jennifer E.,Aube, Jeffrey
, p. 4316 - 4318 (2007/10/03)
Four stereocenters and three rings are established in one step in a new formal synthesis of (±)-stenine (see scheme). This key reaction cascade consists of an intramolecular Diels-Alder reaction followed by an intramolecular Schmidt reaction. The resultin
Etherification of alkoxydialkylsilanes with carbonyl compounds
Jiang, Xinglong,Bajwa, Joginder S,Slade, Joel,Prasad, Kapa,Repi?, Oljan,Blacklock, Thomas J
, p. 9225 - 9227 (2007/10/03)
A novel method for preparing ethers from alkoxydialkylsilanes and carbonyl compounds through reductive etherification is described. The salient feature in this method is the utilization of internal hydrogen as the hydride source for reducing the oxonium intermediate generated by using the Cl(R)2SiBr[BiBr3/Cl(R)2SiH] catalytic system.