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A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.
A regio- and diastereoselective anodic coupling of 3',4',5'-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (-)-thebaine. Expand
Preparation of Indoles from α-Aminonitriles: A Short Synthesis of FGIN-1-27
α-Aminonitriles derived from 2-aminocinnamic acid esters and amides can be cyclized under basic conditions to furnish substituted indole-3-acetic acid derivatives in quantitative yield. The reaction… Expand
Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.
- A. Lipp, Maximilian Selt, D. Ferenc, D. Schollmeyer, S. Waldvogel, T. Opatz
- Chemistry, Medicine
- Organic letters
- 18 February 2019
A fully regio- and diastereoselective electrochemical 4a-2'-coupling of a 3',4',5'-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone, providing high yields and under constant current conditions both in a simple undivided cell or in continuous flow. Expand
Synthesis of the CDK-InhibitorPaullone by Cyclization of a Deprotonated α-Aminonitrile
Cyclization of a deprotonated N-monosubstituted α-aminonitrileobtained by Strecker reaction of a protected 2-amino-benzaldehydewith ethyl 2-aminocinnamate serves as the key step in a short… Expand
Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones
- Murat Kucukdisli, D. Ferenc, Marcel Heinz, C. Wiebe, T. Opatz
- Chemistry, Medicine
- Beilstein journal of organic chemistry
- 24 February 2014
Summary The cyclocondensation of enones with aminoacetonitrile furnishes 3,4-dihydro-2H-pyrrole-2-carbonitriles which can be readily converted to 2,4-disubstituted pyrroles by microwave-induced… Expand
Facile preparation of 3-amino-4-(arylamino)-1H-isochromen-1-ones by a new multicomponent reaction
Reactions between 2-formylbenzoic acid, various anilines and HCN result in the formation of 3-amino-4-(arylamino)-1H-isochromen-1-ones in high yield. The mechanism of this three-component… Expand
An unexpected three-component condensation leading to amino- (3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)- acetonitriles.
These compounds originate from the condensation of 2-carboxybenzaldehyde with the amine and two molecules of hydrogen cyanide and represent a novel class of isoindolinones. Expand
A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine.
The first successful entry toward the curare alkaloids (±)-tubocurine and (±-curine) is permitted by two consecutive Cu-catalyzed Ullmann-type C-O couplings. Expand
Ring Contracting Rearrangements of 3‐Amino‐4‐(arylamino)‐1H‐isochromen‐1‐ones
Two new ring contracting rearrangements of 3-amino-4-(arylamino)-1H-isochromen-1-ones, leading to 1-(arylamino)-3-oxo-1,3-dihydroisobenzofuran-1-carboxamides… Expand
Synthesis of 5‐Fluorocytosine Using 2‐Cyano‐2‐fluoroethenolate as a Key Intermediate
There is an urgent demand for 5-fluorocytosine (5FC) due to its activity against HIV-induced fungal infections as well as its use as a key intermediate in the synthesis of the clinically highly… Expand