Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals

Taking shortcuts: A remarkably short and high-yielding asymmetric total synthesis of (−)-oseltamivir takes advantage of organocatalysis and single-pot domino operations The target, known as the drug Tamiflu, is prepared efficiently in a short time, and also its derivatives can be synthesized effectively

High‐Yielding Synthesis of the Anti‐Influenza Neuramidase Inhibitor (−)‐Oseltamivir by Three “One‐Pot” Operations

In view of the impending transition of chemical industry from depleting fossil raw materials to renewable feedstocks — the end of cheap oil is predicted around 2040 — this account gives an overview on chemically and enzymatically transforming carbohydrates, by far the major part of the annually regrowing biomass, into products with versatile industrial application profiles and the potential to eventually replace those presently derived from petrochemical sources.



The article contains sections titled: 

1.	Introduction	
2.	Availability of Carbohydrates	
3.	Current Nonfood Industrial Products from Sugars	
3.1.	Ethanol	
3.2.	Furfural	
3.3	d-Sorbitol	
3.4	Lactic Acid and Polylactic Acid (PLA)	
3.5.	Sugar-Based Surfactants	
3.5.1.	‘Sorbitan’ Esters	
3.5.2.	N-Methyl-N-acyl-glucamides (NMCA)	
3.5.3.	Alkylpolyglucosides (APG)	
3.5.4.	Sucrose Fatty Acid Monoesters	
3.6.	Pharmaceuticals and Vitamins	
4.	Toward Further Sugar-based Chemicals: Potential Development Lines	
4.1.	Furan Compounds	
4.1.1.	5-Hydroxymethylfurfural (HMF)	
4.1.2.	2,5-Dimethylfuran (DMF)	
4.1.3.	Furans with a Tetrahydroxybutyl Side Chain	
4.2.	Dihydropyrones	
4.3.	Sugar-Derived Unsaturated Nitrogen Heterocycles	
4.3.1.	Pyrroles	
4.3.2.	Pyrazoles	
4.3.3.	Imidazoles	
4.3.4.	3-Pyridinols	
4.4.	Toward Sugar-Based Aromatic Chemicals	
4.5.	Microbial Conversion of Six-Carbon-Sugars into Simple Carboxylic Acids and Alcohols	
4.5.1.	Carboxylic Acids	
4.5.2.	Potential Sugar-Based Alcohol Commodities by Microbial Conversions	
4.6.	Chemical Conversion of Sugars into Carboxylic Acids	
4.7.	Biopolymers from Polymerizable Sugar Derivatives	
4.7.1.	Synthetic Biopolyesters	
4.7.2.	Microbial Polyesters	
4.7.3.	Polyamides	
5.	Outlook	
6.	References

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Carbohydrates as Organic Raw Materials

Significantly Improved Method for the Pd-Catalyzed Coupling of Phenols with Aryl Halides: Understanding Ligand Effects

Metabolic engineering for microbial production of aromatic amino acids and derived compounds.

Practical Total Synthesis of the Anti-Influenza Drug GS-4104

Synthese de cyclodityrosyles a partir des dipeptides lineaires correspondants; ces piperazinediones-2,5 sont ensuite reduites par BH 3 /THF en les bis-arylmethyl-2,5 piperazines chirales correspondantes. Application a la synthese de dibenzyl-2,5 dimethyl-1,4 piperazine a partir de cyclophenylalanyle

Organic chemistry of L-tyrosine. 1. General synthesis of chiral piperazines from amino acids

The 1-pyrrolyl fumarate (5), prepared by condensation of 1-hydroxypyrrole (1a) with trans-3-(methoxycarbonyl)-acryloyl chloride (4), undergoes a facile interamolecular Diels–Alder reaction to give the product (6), the first intramolecular cycloaddition of a pyrrole.

Intramolecular Diels–Alder chemistry of pyrroles

The role of diffuse double-layer calcium in cardiac excitation-contraction coupling was examined using rabbit interventricular septa, cultured neonatal rat myocardial cells, and gas-dissected sarcolemmal membranes. The diffuse double layer refers to the space directly adjacent to the sarcolemma where the ionic composition of the media is a direct function of the membrane surface potential. The divalent cation dimethonium was used as a specific probe for the diffuse double layer. According to Gouy-Chapman theory, replacement of sodium with sucrose should increase the amount of calcium located in this compartment. Dimethonium (10 mM) was found to decrease calcium uptake and contractility during low-sodium (33 mM) perfusion when the perfusate contained sucrose but not LiCl. Dimethonium did not decrease calcium uptake or contractility during control perfusion. The results suggest that calcium present in the myocardial diffuse double layer can be augmented or reduced in accordance with Gouy-Chapman theory. Changes in diffuse double-layer calcium are accompanied by small (7.8%) but significant changes in contractility.

/pdf/contribution-of-myocardial-diffuse-double-layer-calcium-to-46u3hjyjo7.pdf

John C. Rohloff

Papers

Practical Total Synthesis of the Anti-Influenza Drug GS-4104

Organic chemistry of L-tyrosine. 1. General synthesis of chiral piperazines from amino acids

Intramolecular Diels–Alder chemistry of pyrroles

Contribution of myocardial diffuse double-layer calcium to contractile function

Intramolecular diels-alder chemistry of pyrroles