Synthetic pathways to water-soluble phthalocyanines and close analogs

The different types of water-soluble phthalocyanines are presented and their synthesis is reviewed.     

Synthetic approaches to monofluoroalkenes

Monofluoroalkenes are an important fluorinated class of compounds with applications in medicinal chemistry, material sciences and organic chemistry. An overview of methods allowing synthetic access to these fluorinated building blocks is provided. In particular, this critical review, which covers publications up to October 2010, will be divided according to the substitution pattern of the monofluoroalkenes, i.e. di-, tri- or tetra-substituted. Within each group, the various synthetic approaches will be divided according to the reaction type (282 references).     

Synthetic routes to imidazothiazines

This review article presents the available synthetic routes for the preparation of different types of imidazothiazines. Imidazothiazines dealt with are classified into five types based on the position of linkage between imidazole and thiazine rings. The importance of the latter compounds in pharmacology is also discussed. The main purpose of this review is to present a survey of literature on imidazothiazines and provide useful and up-to-date data to organic and medicinal chemist, since such compounds have not been reviewed before.     

Synthetic routes to thiazoloindoles

Several structural types of thiazoloindoles can be distinguished with regard to the position of the fusion between the thiazole, benzene, and pyrrole rings. The present review describes the synthetic routes to five selected types of thiazoloindole derivatives with [3,2-a], [3,4-a], [5,4-b], [5,4-e], and [4,5-e] fusion. These compounds are useful for the discovering of future targets and the development of new drug molecules.     

Synthetic approach to quinocarcin

A basic synthetic route to quinocarcin is elaborated. The optically active basic skeleton of quinocarcin, iminoazepinoisoquinoline 1 was efficiently synthesized starting from phenylalanine and glutamic acid derivative.     

Synthetic Approaches to Selenoesters

Selenoesters are compounds of great synthetic relevance since they can be used in several types of chemical transformations and mainly due to their great capacity in the formation of acyl radicals. Therefore, the scientific community has been developing several methods for the synthesis of this class of molecules. This review will address the synthesis of these compounds from different starting materials, such as carboxylic acids derivatives (acid chlorides and anhydrides), aldehydes, selenoacetylenes and miscellaneous methods.     

Synthetic approaches to new polymers

A plenary lecture should be an introduction into the main topic of the symposium and a review about the state of art. Therefore, in the first part of this presentation different possibilities for the preparation of new polymers are briefly discussed from a chemical point of view. Some selected examples from the literature show how methods of organic chemistry can be utilized for polymer science: new catalytic systems, new monomers, modification of polymers, new poly-reactions. In the second part, several polyelectrolytes are described: polymers with sec., tert. and quart. N-atoms in the main chain, block copolymers and block polyampholytes. The third part deals with the problems of rod-like macromolecules for instance oligo- and poly(p-phenylene)s, poly(p-phenyleneethynylene)s, aromatic polyimides and a new spiroionene.     

Synthetic Route to Ergot Alkaloids

Rye is sometimes infected by a fungus called Claviceps purpurea. The term ergot designates the dark, brown, tuberous bodies which can be collected before or during harvesting and represent one of the most remarkable drugs of our therapeutic arsenal. Actually, the most significant alkaloids are metabolic products of these fungi. We elaborated three alternative total synthetic pathways to construct the ergoline skeleton, one of which – suitable for scaling up – finally resulted in (+)‐lysergic acid ( 32a ) and α‐ergocryptine ( 1 ) (Schemes 5 and 6).     

Improved Synthetic Approach to Tenatoprazole

An improved synthetic approach to tenatoprazole 1 is described. It started from 2,3,5‐trimethyl‐4‐nitropyridine‐N‐oxide 2 with acetic anhydride via rearrangement and hydrolysis to give 3, Chlorination with SOCl₂ yielded 2‐chloromethyl‐3,5‐dimethyl‐4‐nitropyridine hydrochloride 4, then 4 condensed with 2‐mercapto‐5‐methoxy imidazole [4,5‐b]pyridine 5 to give 5‐methoxy‐2‐[(4‐nitro‐3,5‐dimethyl‐2‐pyridinyl)methylthio]imidazole[4,5‐b]pyridine 6. At last the title compound 1 was produced by two methods: 6 was oxidized with MCPBA and then methoxylated with CH₃ONa to give 1 and 6 was first methoxylated with CH₃ONa and then oxidized with MCPBA to give 1. The overall yield is around 26% for both five‐step syntheses.     

Synthetic access to arsenic-containing phosphatidylcholines

We wish to disclose the first synthesis of 1-O-hexadecanoyl-2-O-((15-(dimethylarsinoyl)pentadecanoyl)oxy)-sn-glycero-3-phosphocholine, which belongs to the group of arsenic-containing phosphatidylcholines (AsPCs), recently discovered in herring caviar. The synthesized product will serve as a model compound to study biological and toxicological properties of arsenolipids in food.     

Synthetic approach to anthracyclinone C-glycosides

Stereospecific coupling of a pentadienyl chain to C.1 of daunosamine followed by Diels-Alder reactions with quinones gave a new synthesis of C-glycosides, including the first intermediates to anthracycline C-glycosyl isosteres.     

Novel Synthetic Route to Fluoxetine

Racemic fluoxetine was synthesized from 3-benzoylpropionic acid in five steps in 54% overall yield.     

Synthetic routes to 5,10,15-triaryl-tetrabenzocorroles

Two different synthetic routes for the preparation of 5,10,15-triaryl-tetrabenzocorroles have been developed. The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole and a suitable substrate to form the four β-fused aryl rings. These routes are successful to lead to the target tetrabenzocorroles, obtained in both cases as the corresponding Cu complex and with the highest yield obtained via the one-step cross-coupling methodology. Demetalation of the Cu-tetrabenzocorrole produces the corresponding free base; this macrocycle was further exploited to obtain the Sn and Co complexes in good yields.     

Synthetic Routes to 3-Pyrrolidinol

Short, convenient routes to 3-pyrrolidinol are described.