scholarly journals C–H-Functionalization logic guides the synthesis of a carbacyclopamine analog

2014 ◽  
Vol 10 ◽  
pp. 1564-1569 ◽  
Author(s):  
Sebastian Rabe ◽  
Johann Moschner ◽  
Marina Bantzi ◽  
Philipp Heretsch ◽  
Athanassios Giannis
Keyword(s):  
Chemical Synthesis ◽  
New Class ◽  
Metal Catalyzed ◽  
Acid Stable

The chemical synthesis of carbacyclopamine analog 2, a cyclopamine analog with an all-carbon E-ring, is reported. The use of C–H-functionalization logic and further metal-catalyzed transformations allows for a concise entry to this new class of acid-stable cyclopamine analogs.

Phosphonolipids. XV. Synthesis of a dihydroceramide aminoethylphosphonate

1968 ◽  
Vol 46 (3) ◽  
pp. 525-532 ◽  
Author(s):  
Erich Baer ◽  
Bimal C. Pal
Keyword(s):  
Chemical Synthesis ◽  
Acid Chloride ◽  
Phosphonic Acid ◽  
Steam Distillation ◽  
Free Acid ◽  
Reaction Products ◽  
New Class ◽  
Naturally Occurring ◽  
Benzoyl Group ◽  
Complex Lipids

The first chemical synthesis of a dihydroceramide aminoethylphosphonate is described. It is a saturated representative of a new class of recently discovered, naturally occurring complex lipids derived from phosphonic acid. The compound, viz. erythro-N-palmitoyl-DL-dihydrosphingosyl-1-(2-aminoethyl)-phosphonate, was obtained by two procedures: phosphonylation of erythro-N-palmitoyl-3-O-benzoyl-DL-dihydrosphingosine with (2-N,N-dibenzylammoethyl)phosphonic acid chloride (hydrochloride) and triethylamine, or with (2-phthalimidoethyl)phosphonic acid monochloride and triethylamine, and freeing the reaction products of both procedures, viz. erythro-N-palmitoyl-3-O-benzoyl-DL-dihydrosphingosyl-1-(2-N,N-dibenzylaminoethyl)phosphonate and erythro-N-palmitoyl-3-O-benzoyl-DL-dihydrosphingosyl-1-(2-phthalimidoethyl)phosphonate, from their protective benzyl or phthaloyl group by hydrogenolysis or hydrazinolysis, respectively, followed in both cases by removal of the benzoyl group by saponification.The (2-N,N-dibenzylaminoethyl)phosphonic acid was obtained by treating (2-bromoethyl)phosphonic acid with N,N-dibenzylamine and converting the reaction product, viz. the dibenzylammonium salt of (2-N,N-dibenzylaminoethyl)phosphonic acid, into the free acid by steam distillation.

A new class of HIV-1 protease inhibitor: The crystallographic structure, inhibition and chemical synthesis of an aminimide peptide isostere

1996 ◽  
Vol 4 (9) ◽  
pp. 1545-1558 ◽  
Author(s):  
Earl E. Rutenber ◽  
Fiona McPhee ◽  
Alan P. Kaplan ◽  
Steven L. Gallion ◽  
Joseph C. Hogan ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Protease Inhibitor ◽  
Crystallographic Structure ◽  
New Class ◽  
Hiv 1

scholarly journals Engineering of Reductive Aminases for Asymmetric Synthesis of Enantiopure Rasagiline

2021 ◽  
Vol 9 ◽  
Author(s):  
Kai Zhang ◽  
Yuanzhi He ◽  
Jiawei Zhu ◽  
Qi Zhang ◽  
Luyao Tang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Chemical Synthesis ◽  
Asymmetric Synthesis ◽  
Rational Design ◽  
Enantiomeric Excess ◽  
Industrial Applications ◽  
Viable Alternative ◽  
Environmentally Benign ◽  
Secondary Amines ◽  
Metal Catalyzed

Reductive aminases (RedAms) for the stereoselective amination of ketones represent an environmentally benign and economically viable alternative to transition metal–catalyzed asymmetric chemical synthesis. Here, we report two RedAms from Aspergillus calidoustus (AcRedAm) and bacteria (BaRedAm) with NADPH-dependent features. The enzymes can synthesize a set of secondary amines using a broad range of ketone and amine substrates with up to 97% conversion. To synthesize the pharmaceutical ingredient (R)-rasagiline, we engineered AcRedAm through rational design to obtain highly stereoselective mutants. The best mutant Q237A from AcRedAm could synthesize (R)-rasagiline with >99% enantiomeric excess with moderate conversion. The features of AcRedAm and BaRedAm highlight their potential for further study and expand the biocatalytic toolbox for industrial applications.

scholarly journals Metal Catalyzed Suzuki-Miyaura Cross-Coupling– Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules

2017 ◽  
Author(s):  
Hira Israr ◽  
Shazia Kaousar ◽  
Nasir Rasool ◽  
Gulraiz Ahmad ◽  
Muhammad Nazirul Mubin Aziz ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biologically Active ◽  
Polymer Chemistry ◽  
Active Compounds ◽  
New Class ◽  
Cross Coupling Reaction ◽  
Metal Catalyzed

New class of biologically active and non-active compounds can be synthesized via transition metal mediated Suzuki cross coupling reaction that has a great impact on the advancement of organic chemistry. These resulted products can lend a helping hand in pharmaceutical and polymer chemistry for the betterment of mankind. Suzuki-Miyaura cross coupling reaction is one of the best tools through which many natural and non-natural compounds can be synthesized.

Sign in / Sign up

Export Citation Format

Share Document