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Contents list for Organic & Biomolecular Chemistry, issue 10, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 1693
DOI: 10.1039/b806493h
Inside front cover
Org. Biomol. Chem., 2008, 6, 1694
DOI: 10.1039/b806494f
Contents and Chemical Science
Org. Biomol. Chem., 2008, 6, 1695
DOI: 10.1039/b806495b
Emerging Area
The role of chemical synthesis in structure elucidation of oxasqualenoids
Yoshiki Morimoto,
Org. Biomol. Chem., 2008, 6, 1709
DOI: 10.1039/b801126e
Enhanced HTML article available
In modern structure elucidation of complex and diverse natural products, oxasqualenoids illustrate the importance of chemical synthesis in addition to spectroscopic methods.
Perspective
Catalytic addition of alkyne C–H, amine N–H, and phosphine P–H bonds to carbodiimides: an efficient route to propiolamidines, guanidines, and phosphaguanidines
Wen-Xiong Zhang and Zhaomin Hou,
Org. Biomol. Chem., 2008, 6, 1720
DOI: 10.1039/b800135a
Various metal amidinate–(phospha)guanidinate species can be protonated by alkyne C–H, amine N–H, and phosphine P–H bonds, which leads to catalytic formation of propiolamidines and (phospha)guanidines through addition of RE–H bonds to carbodiimides.
Communications
Stereospecific anti SE2
fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides
Laurence Carroll, Samantha McCullough, Tom Rees, Timothy D. W. Claridge and Véronique Gouverneur,
Org. Biomol. Chem., 2008, 6, 1731
DOI: 10.1039/b803888k
The electrophilic fluorodesilylation of enantioenriched allenylsilanes proceeds with efficient transfer of chirality. The silylation–fluorination of propargylic alcohols occurs with overall retention of stereochemistry, a result consistent with a stereospecific anti SE2 mechanism for the fluorination step.
An efficient method for synthesising unsymmetrical silaketals: substrates for ring-closing, including macrocycle-closing, metathesis
Christopher Cordier, Daniel Morton, Stuart Leach, Thomas Woodhall, Catherine O'Leary-Steele, Stuart Warriner and Adam Nelson,
Org. Biomol. Chem., 2008, 6, 1734
DOI: 10.1039/b804769n
Diisopropylsilyl ethers were activated with N-bromosuccinimide, and reacted with a fluorous-tagged alcohol, to yield tethered substrates for ring-closing metathesis reactions.
Papers
An efficient synthesis of indolo[3,2-a]carbazoles via the novel acid catalyzed reaction of indoles and diaryl-1,2-diones
Vijay Nair, Vidya Nandialath, Keecherikunnel G. Abhilash and Eringathodi Suresh,
Org. Biomol. Chem., 2008, 6, 1738
DOI: 10.1039/b803009j
A mild and efficient one pot method for the synthesis of indolo[3,2-a]carbazole derivatives by the para-toluenesulfonic acid catalyzed condensation of indole with acyclic 1,2-diones is described. With cyclobutene-1,2-diones the reaction afforded indole substituted carbazole derivatives in good yield.
Cyclen-based bismacrocycles for biological anion recognition. A potentiometric and NMR study of AMP, ADP and ATP nucleotide complexation
Anne-Sophie Delépine, Raphaël Tripier and Henri Handel,
Org. Biomol. Chem., 2008, 6, 1743
DOI: 10.1039/b719514a
The behaviour of two cyclen-based bismacrocycles linked by aromatic spacers as receptors of adenosine monophosphate, adenosine diphosphate and adenosine triphosphate anions is explored.
Synthesis and characterization of indolocarbazole-quinoxalines with flat rigid structure for sensing fluoride and acetate anions
Ting Wang, Yu Bai, Liang Ma and Xiu-Ping Yan,
Org. Biomol. Chem., 2008, 6, 1751
DOI: 10.1039/b801447g
Novel indole-based anion sensor with flat rigid structure showed effective recognition for acetate anion through the formation of two hydrogen bonds.
Discovery of a new series of jatrophane and lathyrane diterpenes as potent and specific P-glycoprotein modulators
Elisa Barile, Marianna Borriello, Attilio Di Pietro, Agnès Doreau, Caterina Fattorusso, Ernesto Fattorusso and Virginia Lanzotti,
Org. Biomol. Chem., 2008, 6, 1756
DOI: 10.1039/b800485d
A new series of diterpenes, the jatrophanes euphoscopin M, euphoscopin N and euphornin L, and the lathyrane euphohelioscopin C, were isolated from Euphorbia helioscopia, their stereostructures elucidated and their ability to inhibit P-glycoprotein assessed.
Regiochemistry of the microwave-assisted reaction between aromatic amines and 
-bromoketones to yield substituted 1H-indoles
Yosu Vara, Eneko Aldaba, Ana Arrieta, José L. Pizarro, María I. Arriortua and Fernando P. Cossío,
Org. Biomol. Chem., 2008, 6, 1763
DOI: 10.1039/b719641e
Computational and experimental studies of the Bischler reaction between aromatic amines and -bromoketones have revealed that the substitution pattern of the starting amine can modify significantly the selectivity of the reaction.
Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride
Mie Højer Vilhelmsen, Lars Frøsig Østergaard, Mogens Brøndsted Nielsen and Steen Hammerum,
Org. Biomol. Chem., 2008, 6, 1773
DOI: 10.1039/b800039e Enhanced HTML article available
Reduction of 2-chloro-N-phenylpropanamide with LiAlH4 proceeds to provide a mixture of propyl- and isopropylanilines via non-regioselective ring opening of an aziridine intermediate.
Regioselective intramolecular ring closure of 2-amino-6-bromo-2,6-dideoxyhexono-1,4-lactones to 5- or 6-membered iminuronic acid analogues: synthesis of 1-deoxymannojirimycin and 2,5-dideoxy-2,5-imino-D-glucitol
Birgitte M. Malle, Inge Lundt and Tanja M. Wrodnigg,
Org. Biomol. Chem., 2008, 6, 1779
DOI: 10.1039/b719631h
Syntheses of 1,5-dideoxy-1,5-iminuronic acid mimetics with D-altro, L-altro, D-galacto, L-galacto and D-manno configurations as well as of 2,5-dideoxy-2,5-imino-L-gulonic acid are reported
Rapid generation of macrocycles with natural-product-like side chains by multiple multicomponent macrocyclizations (MiBs)
Daniel G. Rivera, Otilie E. Vercillo and Ludger A. Wessjohann,
Org. Biomol. Chem., 2008, 6, 1787
DOI: 10.1039/b715393g
In the one-pot six-component assembly of peptoid macrocycles with peptide- or sugar-type privileged appendages, the bifunctional reagents are responsible for the size, rigidity and side chain position, and the monofunctional reagents for exocyclic decoration and function.
Cucurbit[7]uril host–guest complexes with small polar organic guests in aqueous solution
Ian W. Wyman and Donal H. Macartney,
Org. Biomol. Chem., 2008, 6, 1796
DOI: 10.1039/b801650j
Cucurbit[7]uril binds small polar organic guests in aqueous solution through a combination of hydrophobic effects and quadrupole–dipole interactions, with alkali metal cation capping(s) of the carbonyl-lined portals reducing the host–guest stability constants.
Synthesis of 3-(2-N,N-diethylaminoethoxy)indoles as potential 5-HT6 receptor ligands
Karolin Alex, Nicolle Schwarz, Vivek Khedkar, Iliyas Ali Sayyed, Annegret Tillack, Dirk Michalik, Jörg Holenz, José Luis Díaz and Matthias Beller,
Org. Biomol. Chem., 2008, 6, 1802
DOI: 10.1039/b802054j
The synthesis of new pharmaceutically interesting 3-(2-N,N-diethylaminoethoxy)indole derivatives is described.
Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method
Hironobu Hojo, Yuichi Murasawa, Hidekazu Katayama, Tsuyoshi Ohira, Yuko Nakahara and Yoshiaki Nakahara,
Org. Biomol. Chem., 2008, 6, 1808
DOI: 10.1039/b800884a
Aryl thioesters of peptide segments were prepared by the Fmoc strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The segments were used for the synthesis of 95-amino acid chemokine CCL-27 by an Ag+-free thioester method.
Synthesis of -cyclodextrin [2]-rotaxanes using chlorotriazine capping reagents
Ryan E. Dawson, Subashani Maniam, Stephen F. Lincoln and Christopher J. Easton,
Org. Biomol. Chem., 2008, 6, 1814
DOI: 10.1039/b802229a
Ten triazine-capped rotaxanes such as the [c2]-daisy chain were prepared as the basis of molecular devices.
Design and synthesis of biotinylated inositol phosphates relevant to the biotin–avidin techniques
Kensaku Anraku, Teruhiko Inoue, Kenji Sugimoto, Takashi Morii, Yasuo Mori, Yoshinari Okamoto and Masami Otsuka,
Org. Biomol. Chem., 2008, 6, 1822
DOI: 10.1039/b719938d Enhanced HTML article available
Six bifunctional molecules containing biotin and various inositol phosphates were synthesized. The building blocks of the inositol moiety were synthesized from optically resolved myo-inositol derivatives and were assembled to the biotin linker through a phosphate linkage.
Synthesis of (-)-conocarpan by two routes based on radical cyclization and establishment of its absolute configuration
Derrick L. J. Clive and Elia J. L. Stoffman,
Org. Biomol. Chem., 2008, 6, 1831
DOI: 10.1039/b801858h
Two independent routes for the total synthesis of the bioactive neolignan (-)-conocarpan are described, confirming the need for revision of the absolute stereochemistry.
-Amino group hydroxylation of L-ornithine during coelichelin biosynthesis
Verena Pohlmann and Mohamed A. Marahiel,
Org. Biomol. Chem., 2008, 6, 1843
DOI: 10.1039/b801016a
The hydroxylation reaction of the -amino group of L-ornithine during the biosynthesis of the siderophore coelichelin is catalyzed by a monooxygenase dependent on FAD, NADPH and molecular oxygen.
Synthesis of imidazolidin-2-one-4-carboxylate and of (tetrahydro)pyrimidin-2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement
Gaetano Angelici, Simone Contaldi, Sarah Lynn Green and Claudia Tomasini,
Org. Biomol. Chem., 2008, 6, 1849
DOI: 10.1039/b801909f
A mild and efficient methodology for the Hofmann rearrangement of protected asparagine and protected glutamine is reported; good results are obtained with a wide selection of protecting groups.
Back matter
Org. Biomol. Chem., 2008, 6, 1853
DOI: 10.1039/b806496m
Back cover
Org. Biomol. Chem., 2008, 6, 1855
DOI: 10.1039/b806497k
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