Mini-Reviews in Organic Chemistry - Volume 1, Issue 1, 2004

Rapid advances in the field of Organic Chemistry have resulted over the last two decades in a growing number of high quality publications. Many of which cannot be published in a timely fashion because of limited number of publication journals with the result that publications of important and urgent nature are often delayed by a year or more. There was, therefore, an acute need of a journal which would publish important mini-reviews rapidly. “Mini-Reviews in Organic Chemistry” is thus being launched to meet this need. Mini- Reviews in Organic Chemistry will cover various dimensions of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition, and physical organic chemistry. The emphasis will be on publishing quality papers very rapidly. The mini-reviews will be processed rapidly taking the full advantage of internet technology for both the submission and review of manuscripts. I am sure the journal is essential reading to all organic chemists in both academia and industry. There will be four issues of this journal published in 2004. The publication frequency of the journal will increase gradually in the years to come. The internationally eminent editorial board including such eminent authorities as A. Attygalle, N. Berova, W. Boland, H. Budzikiewicz, T.R. Burke, R. Caple, Y. Chapleur, D. Crich, H.M.L. Davies, W. Donaldson, K.M. Doxsee, C.J. Easton, El S.H. El Ashry, S.V. Evans, C.G. Frost, F. Fulop, M. Harmata, R.G. Harvey, J.W. Herndon, A.H. Hoveyda, N.S. Isaacs, C.W. Jefford, G. Jenner, Z. Kelman, A.D. Kinghorn, D.G.I. Kingston, G. Kirsch, W. Kitching, A. Krief, M.E. Kuehne, S.V. Ley, C.-J. Li, R.J. Linhardt, H.-w. Liu, J. Meinwald, M. Miyazawa, S. Mobashery, C.J. Moody, K. Mori, P. Neri, T. Okuda, F.L. Ortiz, H.M.I. Osborn, L.A. Paquette, B.S. Paulsen, P. Potier, S.G. Pyne, E. Roeder, V.M. Rotello, T.K. Sawyer, R.R. Schmidt, P.H. Seeberger, M. Sekine, G. Sello, M.A. Sierra, I.P. Smoliakova, B.B. Snider, K. Soai, T. Sugai, M.D. Threadgill, P. Vogel, P.G. Wang, R.M. Williams, Z.J. Witczak, Y. Yamamoto and K.P. Zeller will undoubtedly guide me in the editorial responsibilities and ensure the very highest standards. The opinions expressed by six Nobel Laureates can be reviewed at www.bentham.org / nobel which reflect the excellent reputation that Bentham Science Publishers enjoy. I keenly look forward to the wide acceptance of this new journal by the community of organic chemists.

Indium(III) salts have received considerable attention as Lewis acids in recent years. Their stability to co-ordinating atoms present in organic substrates makes them excellent catalysts in substoichiometric quantities. Stability in water allows aqueous recycling and often the use of water as a reaction solvent. This review will focus on describing new developments in the application of indium catalysts in synthetic organic chemistry. Transformations that will be covered include aromatic functionalisation, cycloaddition reactions, conjugate additions and multi-component coupling reactions.

As a thermodynamical parameter, pressure modifies the physical and physicochemical properties of liquids considered as media for organic synthesis. In a first part, the review details the effect of pressure on solubility, freezing point, and viscosity. The second paragraph examines the pressure effects on solute-medium interactions associated with volume changes. There are two main pressure-sensitive interactions: electrostatic and solvophobic interactions. i) Considering electrostrictive effects, the pressure rate acceleration is highest in apolar media. This is illuminated by many examples taken from unimolecular reactions, [4+2] and [2+2] cycloadditions, Michael reactions, Menshutkin quaternisations, Morita-Baylis-Hillman additions. ii) Pressure reduces the magnitude of solvophobic (hydrophobic, fluorophobic), interactions meaning less pressure sensitivity of reaction rates. In the last part, future high pressure media are outlined i.e. supercritical fluids and ionic liquids. However, the results reported to date do not permit to draw a clear conclusion. High pressure synthetic applications are described in the light of the above emphasized effects. The results presented in the review should allow a judicious choice of the right medium for a rational design of a liquid phase organic synthesis under pressure.

Combinatorial chemistry has contributed to the preparation of biologically important oligosaccharide and glycoconjugate libraries, with a view of improving our understanding of the complex interaction between the carbohydrates and their proteinbased receptors. The combinatorial carbohydrate synthesis strategies, developed in the past decade, provide access to small and medium size libraries. This mini review critically examines both the solution phase and solid phase strategies that have been reported to date.

This review provides a discussion of recent developments in the asymmetric hetero Diels-Alder reaction (AHDAR), with particular emphasis on the synthesis of carbohydrates, their derivatives, and inhibitors of carbohydrate processing enzymes.

Several efficient catalytic aldehyde olefination reactions reported, since the late 1980s, are described. This paper deals with the results obtained with several metals. The reaction conditions, selectivities and the yields obtained are presented. Furthermore, the mechanisms suggested by the different authors are discussed in some detail.

1,2-Oxaphosphetanes are well established intermediate species in the Wittig reaction. Initially, isolable 1,2-oxaphosphetanes represented a source of structural information aimed at supporting mechanistic studies. The evolution of the subject allows the envisaging of stable 1,2-oxaphosphetanes as precursors for the stereoselective formation of olefins.

Asymmetric diols can be used in organic synthesis as chiral synthons or auxiliaries. These two uses show different scopes. In the first case the compound substructure must be present in the final product and, consequently, the possibilities are limited by the number of the possible targets. In the second case the number of variables is greater and the combinations are virtually infinite. In this respect, the use of enantiopure diols has found large coverage, also favored by the availability of enzymatically prepared substrates. In this review we will focus on the use of a special subclass of diols, those derived from naphthalene precursors. An account of both uses will be presented, taking special care of the potential future developments. In addition, a brief account on the preparation methodology of enantiopure 1,2-dihydro-1,2- dihydroxy naphthalenes will be presented.

Direct enzymatic methods for the preparation of enantiopure cyclic β-amino acids (e.g. cispentacin) and β-lactams through the enzyme-catalyzed enantioselective ring opening of β-lactams in water and organic solvents are reviewed. Indirect methods through the lipase-catalyzed asymmetric acylation of N-hydroxymethylated β-lactams or the lipase-catalyzed hydrolysis of the corresponding ester derivatives, followed by ring opening, are also surveyed.

Monolayer-protected nanoparticles represent a new class of receptors, capable of high affinity, multivalent binding with biomolecules. Networks of self-optimizing bioactive substituents can be introduced via facile place-exchange of functionalized thiols, approximating the diversified topology of biological surfaces. Extension of these particles to model systems and in catalysis is described.

The induction of the phase II drug-metabolizing enzyme, NAD(P)H:quinone reductase (QR), using Hepa 1c1c7 hepatoma cells, is currently used as a key member of a panel of in vitro bioassays in our program directed towards the discovery of new plantderived cancer chemopreventive agents. Among a group of natural products, which have been studied as QR inducers are the withanolides, which constitutes about 400 C28 ergostane-type steroids found mainly in approximately 10 genera of the plant family Solanaceae. New withanolides have been isolated and characterized in our recent work on Physalis philadelphica (tomatillo), which is used as a vegetable and condiment in Mexican and Central American cuisine. A further study on Deprea subtriflora has led to the discovery of a new class of C-18 norwithanolides with only 27 carbons in their skeleton. Preliminary structure-activity relationships have been determined for the in vitro induction of QR by members of the withanolide and norwithanolide classes.

Two new approaches for SNP genotyping are described. The one is based on tandem site-selective RNA scission and the genotype is determined by MALDI-TOF / MS analyses of clipped short RNA. The other is visual SNP genotyping with combinations of peptide nucleic acid (PNA) and single-stranded DNA specific nucleases.