Synthesis of Biologically Relevant Molecules

Matthijs J. van Lint, Eelco Ruuter, and Romano V.A. Orru 

Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, Amsterdam, The Netherlands 

As in many aspects of contemporary organic synthesis, catalysis plays a key role in many MBFTs toward biologically relevant molecules (BRMs). Recently developed catalytic methodologies allow novel types of C-C bond formations and/or unprecedented control over the stereochemical outcome of the reaction. On the other hand, multicomponent reactions (MCRs), combining three or more reactants in a one-pot process to give a single product (and therefore inherently MBFTs), 

Stereoselective Multiple Bond-Forming Transformations in Organic Synthesis, First Edition. Edited by Jean Rodriguez and Damien Bonne. 

This chapter is by no means comprehensive, but rather aims to demonstrate the scope and synthetic potential of the above-mentioned classes of MBFTs in the synthesis of BRMs, with illustrative examples ranging from natural products to complex pharmaceuticals. 

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For a comprehensive review on the use of metathesis for the synthesis of complex organic molecules, see J. A. Love, Olefin Metathesis Strategies in the Synthesis of Biologically Relevant Molecules, in Handbook of Metathesis, Vol. 2, R. H. Grubbs, Ed., Wiley-VCH Weinheim, Germany, 2003, pp. 296-360. 

Considerable efforts made for the synthesis of biologically relevant molecules by means of asymmetric phase-transfer catalysis are summarized in this chapter. Because the phase-transfer reaction is usually insensitive to the contamination of air, moisture, and even acidic or inorganic-salt impurities, and it is set up with simple and user-friendly protocols. It is recognized as one of the easiest methods for large-scale, stereoselective production of functional molecules as exemplified by the studies reported from pharmaceutical companies. In addition, ready accessibility of chiral onium salts as a catalyst facilitates an initial trial in... 

Synthesis of clusters inside the cavities of biologically relevant molecules as well as biomolecules in this method, gold ions are sequestered into the cavities of biomolecules and are subsequently reduced into gold clusters. 

The asymmetric acylation reaction has proven utility in the synthesis of biologically relevant targets. This is demonstrated by the plethora of applications of lipases and esterases in total syntheses [ 1 ]. While these enzymes often display superb selectivities, their application to a broad class of substrates may be difficult and unpredictable [2]. To increase access to these materials in optically pure form, over the past decade several groups have developed small molecule catalysts for the asymmetric acylation reaction [3,4], In addition, these catalysts... 

In virtually all experiments that simulate the synthesis of a primordial soup, enantiomers of amino acids and sugars do not occur instead only racemates have been produced (Miller 1953). It is difficult to imagine how only one of the enantiomers formed under the conditions of a primordial broth. Instead, import and identification of biologically relevant molecules in meteorites and comets appears as a more straightforward path. The compounds found in a meteorite provide a natural record of prebiotic chemistry in the early solar system and is closest to the onset of life. 

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