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29 September 2008
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24 September 2008
Drawing together the best content from all RSC publications, to provide a snapshot of the latest developments across the chemical sciences.
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Contents list for Organic & Biomolecular Chemistry, issue 20, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 3629
DOI: 10.1039/b816332b
Contents and Chemical Science
Org. Biomol. Chem., 2008, 6, 3631
DOI: 10.1039/b816333m
Perspective
-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(II)
Ian J. S. Fairlamb,
Org. Biomol. Chem., 2008, 6, 3645
DOI: 10.1039/b811772a
Alkene ligands exert interesting properties on Pd(0) and Pd(II) species, which can be exploited in catalytic processes.
Communications
Synthesis of 8-bromo-, 8-methyl- and 8-phenyl-dATP and their polymerase incorporation into DNA
Hana Cahová, Radek Pohl, Lucie Bednárová, Kate
ina Nováková, Josef Cva
ka and Michal Hocek,
Org. Biomol. Chem., 2008, 6, 3657
DOI: 10.1039/b811935j
Base-modified dATP derivatives bearing Br, Me or Ph groups in position 8 were prepared and tested as substrates for DNA polymerases. While the 8-Br- and 8-Me-dATP were incorporated in primer extensions, the 8-Ph-dATP was not.
Design and synthesis of intrinsically cell-penetrating nucleopeptides
Piero Geotti-Bianchini, Julien Beyrath, Olivier Chaloin, Fernando Formaggio and Alberto Bianco,
Org. Biomol. Chem., 2008, 6, 3661
DOI: 10.1039/b811639c
Nucleopeptides, based on 
-amino acids bearing nucleobases at their side chains, are able to cross the cell membranes and, remarkably, to reach the nucleus without showing cytotoxic effects.
Rapid diastereocontrolled synthesis of 2,2,5-trisubstituted pyrrolidines
Nandkishkor Chandan and Mark G. Moloney,
Org. Biomol. Chem., 2008, 6, 3664
DOI: 10.1039/b811642c
A highly diastereoselective conversion of pyroglumate to 2,2-trisubstituted pyrrolidines is reported. Some compounds exhibit antibacterial activity against S. aureus and E. coli.
Electrophile-induced bromocyclization of 
,
-unsaturated ketimines to intermediate 1-pyrrolinium salts and their selective conversion into novel 5-alkoxymethyl-2-aryl-3-chloropyrroles and 2-aroylpyrroles
Matthias D'hooghe, Christophe Buyck, Jan Contreras and Norbert De Kimpe,
Org. Biomol. Chem., 2008, 6, 3667
DOI: 10.1039/b813890g
Treatment of 2-aryl-5-bromomethyl-3,3-dichloro-1-pyrrolinium bromides with alkoxide afforded 5-alkoxymethyl-2-aryl-3-chloropyrroles, whereas treatment with sodium hydroxide resulted in 2-aroylpyrroles via intermediate aziridines.
Highly efficient formation of halodiazoacetates and their use in stereoselective synthesis of halocyclopropanes
Hanne Therese Bonge, Benjamin Pintea and Tore Hansen,
Org. Biomol. Chem., 2008, 6, 3670
DOI: 10.1039/b814374a
Halogenated analogues of ethyl diazoacetate are synthesised by a novel and highly efficient procedure and give halocyclopropanes in good to excellent yields when exposed to a Rh(II) catalyst in the presence of alkenes.
Papers
New synthetic routes to optically active -quaternary -aryl amino acid derivatives via the diastereoselective Stevens and Sommelet–Hauser rearrangements
Eiji Tayama, Kiwako Orihara and Hiroshi Kimura,
Org. Biomol. Chem., 2008, 6, 3673
DOI: 10.1039/b811162f
Synthetic routes to optically active -quaternary -aryl amino acid derivatives via the diastereoselective Stevens and Sommelet–Hauser rearrangements are presented.
Novel tetrahydrofuran structures derived from 
–-coupling reactions involving sinapyl acetate in Kenaf lignins
Fachuang Lu and John Ralph,
Org. Biomol. Chem., 2008, 6, 3681
DOI: 10.1039/b809464k
Lignification using acetylated monolignol 2 (in Kenaf) produces novel tetrahydrofurans 4–5, as evidenced by degradative methods, and NMR of the lignin polymer.
Interaction of Ca2+ with uracil and its thio derivatives in the gas phase
Cristina Trujillo, Al Mokhtar Lamsabhi, Otilia Mó, Manuel Yáñez and Jean-Yves Salpin,
Org. Biomol. Chem., 2008, 6, 3695
DOI: 10.1039/b810418b
The relative stability of the different tautomers of uracil and its thio-derivatives changes completely upon Ca2+ association, the enolic tautomers becoming the most stable species. Furthermore, Ca2+ has an important catalytic effect on the corresponding tautomeric processes.
Potent HIV-1 protease inhibitors incorporating meso-bicyclic urethanes as P2-ligands: structure-based design, synthesis, biological evaluation and protein–ligand X-ray studies
Arun K. Ghosh, Sandra Gemma, Jun Takayama, Abigail Baldridge, Sofiya Leshchenko-Yashchuk, Heather B. Miller, Yuan-Fang Wang, Andrey Y. Kovalevsky, Yashiro Koh, Irene T. Weber and Hiroaki Mitsuya,
Org. Biomol. Chem., 2008, 6, 3703
DOI: 10.1039/b809178a
A series of novel HIV-1 protease inhibitors incorporating bicyclic meso-1,3-dioxolane and 1,4-dioxane derivatives as P2-ligands is described. Compound 3 has shown remarkable potency.
High physiological thermal triplex stability optimization of twisted intercalating nucleic acids (TINA)
Niels Bomholt, Amany M. A. Osman and Erik B. Pedersen,
Org. Biomol. Chem., 2008, 6, 3714
DOI: 10.1039/b808564a
Increasing the aromatic surface of the lead TINA monomer led to the highest thermal stability, Tm = 30.0 °C, at pH 7.2 observed for bulge insertion of a TINA monomer into a DNA triplex.
Application of iridium catalyzed allylic substitution reactions in the synthesis of branched tryptamines and homologues via tandem hydroformylation–Fischer indole synthesis
Bojan P. Bondzic, Andreas Farwick, Jens Liebich and Peter Eilbracht,
Org. Biomol. Chem., 2008, 6, 3723
DOI: 10.1039/b809143a
Combination of enantioselective Ir catalyzed allylation and a tandem hydroformylation–Fischer indole synthesis sequence proved to be an efficient and highly diversity-oriented method for the synthesis of enantiopure tryptamines and homologues.
Synthesis and biological investigations of tetrakis(p-carboranylthio-tetrafluorophenyl)chlorin (TPFC)
Erhong Hao, Elisabetta Friso, Gianni Miotto, Giulio Jori, Marina Soncin, Clara Fabris, Martha Sibrian-Vazquez and M. Graça H. Vicente,
Org. Biomol. Chem., 2008, 6, 3732
DOI: 10.1039/b807836j
The total synthesis and biological properties of a new carboranyl-containing chlorin (TPFC) are described. TPFC was found to be non-toxic in the dark, but showed extensive photosensitizing ability both in vitro and in vivo.
Solid-phase synthesis and evaluation of TAR RNA targeted -carboline–nucleoside conjugates
Peng Zhao, Hong-Wei Jin, Zhen-Jun Yang, Liang-Ren Zhang and Li-He Zhang,
Org. Biomol. Chem., 2008, 6, 3741
DOI: 10.1039/b809598a
-Carboline–nucleoside conjugate 13 can fit to the UCU three-nucleotide bulge region of TAR RNA. The computer modeling is in good agreement with the experimental data.
Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol
Caroline Aciro, Timothy D. W. Claridge, Stephen G. Davies, Paul M. Roberts, Angela J. Russell and James E. Thomson,
Org. Biomol. Chem., 2008, 6, 3751
DOI: 10.1039/b808811j
A highly chemo- and diastereoselective, metal-free, ammonium-directed dihydroxylation protocol applicable to tertiary, secondary and primary allylic amines has been established.
Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol
Caroline Aciro, Stephen G. Davies, Paul M. Roberts, Angela J. Russell, Andrew D. Smith and James E. Thomson,
Org. Biomol. Chem., 2008, 6, 3762
DOI: 10.1039/b808812h
A metal-free synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol (in >98% de in each case) has been developed.
Reactions of orthophthalaldehyde with ammonia and 2-aminoethanol
Eliona Kulla and Petr Zuman,
Org. Biomol. Chem., 2008, 6, 3771
DOI: 10.1039/b807714m
It is the carbinolamine that forms the isoindole ring. The dehydration yielding the imine is a competitive side reaction.
Oligonucleotide conjugation to a cell-penetrating (TAT) peptide by Diels–Alder cycloaddition
Victoria Steven and Duncan Graham,
Org. Biomol. Chem., 2008, 6, 3781
DOI: 10.1039/b807843b
A series of dienyl-modified oligonucleotides have been synthesised and their reactivity in the Diels–Alder reaction with a maleimido-modified cell-penetrating (TAT) peptide has been observed.
Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species
Tsutomu Sato, Atsushi Kigawa, Ryosuke Takagi, Tomomi Adachi and Tsutomu Hoshino,
Org. Biomol. Chem., 2008, 6, 3788
DOI: 10.1039/b808513g
A novel cyclic C35-terpene was obtained from nonpathogenic Mycobacterium species. This would be the first example of the biosynthesis of a natural terpene via the cyclisation of a linear C35-isoprenoid.
Indene-based scaffolds. Design and synthesis of novel serotonin 5-HT6 receptor ligands
Ermitas Alcalde, Neus Mesquida, Jordi Frigola, Sara López-Pérez and Ramon Mercè,
Org. Biomol. Chem., 2008, 6, 3795
DOI: 10.1039/b808641a
Starting from (Z)-arylmethylideneindenes I, scaffold selection of simple indenylsulfonamides II gave access to novel serotonin 5-HT6 receptor ligands, showing Ki values as low as 20.2 nM.
Phorbasins G–K: new cytotoxic diterpenes from a southern Australian marine sponge, Phorbas sp.
Hua Zhang, Jodie M. Major, Richard J. Lewis and Robert J. Capon,
Org. Biomol. Chem., 2008, 6, 3811
DOI: 10.1039/b808866g
A southern Australian marine sponge, Phorbas sp., has yielded phorbasins G–K, new diterpenes possessing a rare carbon skeleton. Phorbasins display potent and selective activity against a panel of human cancer cell lines, and undergo solvolysis on storage to yield Michael adducts. Structures of natural products and adducts were solved by detailed spectroscopic analysis.
High yielding selective access to spirocyclopropanated 5-oxopiperazine-2-carboxylates and 1,4-diazepane-2,5-diones from methyl 2-chloro-2-cyclopropylideneacetate
Michael Limbach, Vadim S. Korotkov, Mazen Es-Sayed and Armin de Meijere,
Org. Biomol. Chem., 2008, 6, 3816
DOI: 10.1039/b809174a
The title compounds can be prepared selectively and in high yields from methyl 2-chloro-cyclopropylideneacetate ( 1). They can be further transformed into peptide mimics like 11, which contains a DGR motif.
Synthesis and biological evaluation of bile acid dimers linked with 1,2,3-triazole and bis--lactam
Namdev S. Vatmurge, Braja G. Hazra, Vandana S. Pore, Fazal Shirazi, Mukund V. Deshpande, Sreenath Kadreppa, Samit Chattopadhyay and Rajesh G. Gonnade,
Org. Biomol. Chem., 2008, 6, 3823
DOI: 10.1039/b809221d
Novel cholic acid and deoxy cholic acid dimers linked through 1,2,3-triazole and bis--lactam have been synthesised. The antifungal and antibacterial activities of these dimers are presented.
Stannyl ceramides as efficient acceptors for synthesising -galactosyl ceramides
José Antonio Morales-Serna, Yolanda Díaz, M. Isabel Matheu and Sergio Castillón,
Org. Biomol. Chem., 2008, 6, 3831
DOI: 10.1039/b809570a
The use of galactosyl donors with diverse leaving groups for the chemo- and stereoselective glycosylation of stannyl-ceramides in the presence of different promoters is demonstrated.
PNA based artificial nucleases displaying catalysis with turnover in the cleavage of a leukemia related RNA model
Merita Murtola and Roger Strömberg,
Org. Biomol. Chem., 2008, 6, 3837
DOI: 10.1039/b810106j
PNA based artificial nucleases (PNAzymes) cleave a bulge-forming RNA in a catalytic fashion with turnover of substrate and only upon base-pairing with the substrate.
A photo-responsive hydrogelator having gluconamides at its peripheral branches
Yuuki Sako and Yutaka Takaguchi,
Org. Biomol. Chem., 2008, 6, 3843
DOI: 10.1039/b810900a
A newly designed hydrogelator, an anthracene derivative having gluconamides at its peripheral branches, formed a photo-responsive hydrogel. The gel-to-sol transition of the hydrogel was caused by the regioselective photodimerization of the anthracene moiety of the gelator.
Electronically varied quinazolinaps for asymmetric catalysis
Aoife C. Maxwell, Celine Franc, Laurent Pouchain, Helge Müller-Bunz and Patrick J. Guiry,
Org. Biomol. Chem., 2008, 6, 3848
DOI: 10.1039/b810936b
Electronically varied Quinazolinap ligands were prepared, resolved and applied in the Rh-catalysed hydroboration of vinylarenes and the Pd-catalysed allylic alkylation reaction with optimal ees of 92% and 94%, respectively.
Synthetic and biological studies on the spiro-mamakone system
Annabel C. Murphy, Sean R. A. Devenish, Andrew C. Muscroft-Taylor, John W. Blunt and Murray H. G. Munro,
Org. Biomol. Chem., 2008, 6, 3854
DOI: 10.1039/b812263f
An exploration of the chemistry of the spiro-mamakone system, exemplified by the cytotoxic, fungal metabolite spiro-mamakone A, is presented.
Back cover
Org. Biomol. Chem., 2008, 6, 3863
DOI: 10.1039/b816334k
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