15777-86-3Relevant academic research and scientific papers
Concise synthesis of the bioactive natural polyhydroxynaphthoate parvinaphthol B via Hauser-Kraus annulation
Ahn, Sungwan,Han, Young Taek
, p. 4779 - 4780 (2017)
Herein, we describe the first total synthesis of parvinaphthol B, a polyhydroxynaphthoate derived from the root of Pentas parvifolia which exhibits cytotoxic effects against the TNBC cell line. The key feature of the synthesis involves a Hauser-Kraus annulation to provide the polyhydroxynaphthoate skeleton. The synthesis requires only six linear steps and afforded the product in 26.5% overall yield, thus representing a simple method for the further preparation of analogs and biological studies.
Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
, p. 4087 - 4101 (2019/04/30)
The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
Branch-selective, Iridium-catalyzed hydroarylation of monosubstituted alkenes via a cooperative destabilization strategy
Crisenza, Giacomo E. M.,McCreanor, Niall G.,Bower, John F.
supporting information, p. 10258 - 10261 (2014/08/05)
Highly branch-selective, carbonyl-directed hydroarylations of monosubstituted alkenes are described. The chemistry relies upon a cationic Ir(I) catalyst modified with an electron deficient, wide bite angle bisphosphine ligand. This work provides a regioisomeric alternative to the Murai hydroarylation protocol.
Convergent synthesis of pancratistatin from piperonal and xylose
Dam, Johan Hygum,Madsen, Robert
experimental part, p. 4666 - 4673 (2009/12/05)
A synthesis of the antitumour agent pancratistatin is described from piperonal and D-xylose. Piperonal is converted into cinnamyl bromide 11 while methyl 5-iodoribofuranoside 12 is derived from xylose, The allylic bromide and the iodocarbohydrate are combined in a zinc-mediated tandem reaction to afford a highly functionalised 1,7-diene, which is then converted into the corresponding cyclohexene by ring-closing olefin metathesis. Subsequent Overman rearrangement, dihydroxylation and deprotection afford the natural product in a total of 25 steps from, the two starting materials. The longest linear sequence is from piperonal and gives rise to pancratistatin in 18 steps and 7.0% overall yield. Wiley-VCH Verlag GmbH & Co. KGaA.
A chemoenzymatic total synthesis of ent-narciclasine
Matveenko, Maria,Banwell, Martin G.,Willis, Anthony C.
, p. 4817 - 4826 (2008/09/21)
The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the aminoconduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone
Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures
Nery, Marcelo S.,Ribeiro, Renata P.,Lopes, Claudio C.,Lopes, Rosangela S. C.
, p. 272 - 276 (2007/10/03)
A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.
Synthesis of pentasubstituted benzamides via orthometallation: Base and substituent effects
Khaldi, Mustapha
, p. 7 - 13 (2007/10/03)
The synthesis of diversely substituted ori/io-methyl JV,./V-diethylbenzamides using the orthometallation concept is described. A dramatic effect of the substituents and the additive TMEDA is observed during metallation ortho to the N1N-diethylcarboxamido group. Molecular modeling confirms the conformational effect of substituents. A role for the TMEDA additive is proposed. Elscvier,.
Herbicidal 2-(2-imidazolin-2-yl)-benzo-(5-membered)-heterocycles and the use thereof
-
, (2008/06/13)
There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzo-(5-membered)-heterocyclic compounds and derivatives thereof and a method for the use therewith to control monocotyledenous and dicotyledenous plant species.
Synthesis of pancratistatin models
Lopes,Lopes,Heathcock
, p. 6775 - 6778 (2007/10/02)
Two model syntheses for the phenanthridone core of the cytotoxic alkaloid pancratistatin are reported. The key maneuver in these syntheses is 1,4-addition of an ortho-lithiated benzamide derivative to 1-nitrocyclohexene. The resulting 2-aryl-1-nitrocyclohexanes (6 and 11) are further transformed into the pancratistatin models 2 and 3.
