Org. and Biomol. Chem.

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A hydrazide-anchored dendron scaffold for chemoselective ligation strategies

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7290-7296
DOI: 10.1039/C4OB00870G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Liz O'Donovan, Paul A. De Bank
We report the design and synthesis of a dendron scaffold, enabling the chemoselective decoration of target molecules with multiple copies of functional species, such as peptides, via a hydrazone bond.
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Synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via cascade reactions of N-alkyl-N-methacryloyl benzamide with aryl aldehydes

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01442A, CommunicationWannian Zhao, Ping Xie, Min Zhang, Ben Niu, Zhaogang Bian, Charles Pittman, Aihua Zhou
A cascade reaction between N-alkyl-N-methacryloylbenzamide and aryl aldehydes was developed to generate isoquinoline-1,3(2H,4H)-dione derivatives.
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Iridium-catalyzed C-H borylation of pyridines

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7318-7327
DOI: 10.1039/C4OB01565G, PaperScott A. Sadler, Hazmi Tajuddin, Ibraheem A. I. Mkhalid, Andrei S. Batsanov, David Albesa-Jove, Man Sing Cheung, Aoife C. Maxwell, Lena Shukla, Bryan Roberts, David C. Blakemore, Zhenyang Lin, Todd B. Marder, Patrick G. Steel
Iridium-catalysed C-H borylation is an efficient method for the preparation of pyridyl and related azinyl boronate esters.
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Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7270-7278
DOI: 10.1039/C4OB00734D, PaperB. Lygo, M. J. Palframan, G. Pattenden
DFT calculations probing potential cycloaddition pathways leading to the polycyclic ring systems found in the coral secondary metabolites plumarellide, mandapamate and rameswaralide are described.
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Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one ([small beta]-lactam), involving a cascade sequence of reactions as a key step

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7389-7396
DOI: 10.1039/C4OB00948G, PaperDipak Kumar Tiwari, Kishor Chandra Bharadwaj, Vedavati G. Puranik, Dharmendra Kumar Tiwari
A divergent, short, and novel total synthesis of 1,6,8a-tri-epi-castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed.
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Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of vinylogous carbonates

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7397-7409
DOI: 10.1039/C4OB01387E, PaperSantosh J. Gharpure, V. Prasath
C-fused pyranoheterocycles can be assembled in a highly diastereoselective manner using an intramolecular oxa-Pictet-Spengler type reaction of vinylogous carbonates.
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Linear versus branched poly-lysine/arginine as polarity enhancer tags

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7194-7196
DOI: 10.1039/C4OB01354A, CommunicationMarta Paradis-Bas, Maria Albert-Soriano, Judit Tulla-Puche, Fernando Albericio
The design and synthesis of Lys- and Arg-containing peptides as solubilizing tags were studied to evaluate their influence on polarity.
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A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7381-7388
DOI: 10.1039/C4OB00642A, PaperXiaofeng Ma, Qin Tang, Jun Ke, Jichao Zhang, Xinglong Yang, Xudong Shen, Huawu Shao
A highly diastereoselective synthesis method for 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives from 2-C-branched sugars via a neighboring group participation strategy was developed.
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Cooperative hybridization of [gamma]PNA miniprobes to a repeating sequence motif and application to telomere analysis

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7345-7354
DOI: 10.1039/C4OB00953C, PaperHa H. Pham, Connor T. Murphy, Gopalsamy Sureshkumar, Danith H. Ly, Patricia L. Opresko, Bruce A. Armitage
High affinity [gamma]PNA oligomers hybridize cooperatively on telomeric DNA and provide bright fluorescent signals.
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First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7338-7344
DOI: 10.1039/C4OB01470G, PaperChaolei Wang, Guoxiang Wei, Xue Yang, Hequan Yao, Jieyun Jiang, Jie Liu, Mingqin Shen, Xiaoming Wu, Jinyi Xu
The first total synthesis of S-(+)-XJP and R-(-)-XJP has been achieved via intramolecular Heck reaction. A latent functionality strategy was implemented to circumvent the racemization in this endeavor.
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New Ganglio-tripod Amphiphiles (TPAs) for Membrane Protein Solubilization and Stabilization: Implications for Detergent Structure-Property Relationships

7 September, 2014 - 22:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01375A, PaperPil Seok Chae, Hyoung Eun Bae, Hazrat Hussain, Muhammad Ehsan, Jin Woong Kim
Detergents are widely used for membrane protein research; however, membrane proteins encapsulated in micelles formed by conventional detergents tend to undergo structural degradation, necessitating the development of new agents with...
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Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides

7 September, 2014 - 22:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01405G, CommunicationTatina Madhubabu, Anil Kumar Kusunuru, syed khalid Yousuf, debaraj mukherjee
Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated alkynes. Different glycosyl donors such as glycals and anomeric acetates were tested towards alkynyl zinc reagent obtained...
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Pd(II)-Catalyzed Ligand Controlled Synthesis of Pyrazole-4-carboxylates and Benzo[b]thiophene-3-carboxylates

7 September, 2014 - 22:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01576B, PaperYogesh Daulat Dhage, Hiroki Daimon, Cheng Peng, Taichi Kusakabe, Keisuke Takahashi, Yuichro Kanno, Yoshio Inouye, Keisuke Kato
Cyclization-carbonylation of [small alpha],[small beta]-Alkynic hydrazones and (o-alkynylphenyl) (methoxymethyl) sulfides with Pd(tfa)2 in DMSO / MeOH afforded methyl pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates, respectively, in good yields. A simple change of ligand (solvent) allowed...
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Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01611D, PaperKah-Yee Li, Jianbing Jiang, Martin D. Witte, Wouter W. Kallemeijn, Wilma E. Donker-Koopman, Rolf G. Boot, Johannes M. F. G. Aerts, Jeroen D. C. Codee, Gijsbert A. van der Marel, Herman S. Overkleeft
Of six cyclophellitol analogues, the N-pentylaziridine is the most effective retaining human beta-glucosidase inhibitor considering potency and compound stability.
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Palladium-catalyzed carbonylation of halo arene-cis-dihydrodiols to the corresponding carboxylates. Access to compounds unavailable by toluene dioxygenase-mediated dihydroxylation of the corresponding benzoate esters

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01417K, PaperJordan Froese, Jason Reed Hudlicky, Tomas Hudlicky
Compounds of high synthetic value were produced in a much more efficient manner than was previously possible through fermentation.
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68Ga based probe for Alzheimer's disease: synthesis and preclinical evaluation of homodimeric chalcone in [small beta]-amyloid imaging

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,7328-7337
DOI: 10.1039/C4OB00941J, PaperKanchan Chauhan, Anupama Datta, Anupriya Adhikari, Krishna Chuttani, Ajai Kumar Singh, Anil K. Mishra
68Ga complex of chalcone-based bivalent ligand as a potential candidate for cost-effective PET imaging of Alzheimer's disease: a new perspective.
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Facile synthesis of 5-hydroxy-L-lysine from D-galactose as a chiral-precursor

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,7310-7317
DOI: 10.1039/C4OB01220H, PaperLina Guo, Taibao Liu, Kai Chen, Tianbang Song, Peng George Wang, Wei Zhao
A concise synthesis of (2S,5R) and (2S,5S)-5-hydroxy-lysine was achieved by utilizing D-galactose as a chiral-precursor with stereo retention. Using the diazido intermediate, the derived [small beta]-D-galactopyranosyl and [small alpha]-D-glucopyranosyl-(1[rightward arrow]2)-[small beta]-D-galactosyl moieties were synthesized.
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Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,7257-7260
DOI: 10.1039/C4OB01188K, PaperB. V. Subba Reddy, S. Gopal Reddy, M. Ramana Reddy, Manika Pal Bhadra, A. V. S. Sarma
A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a Prins/pinacol cascade.
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Benzodithiophene based [small pi]-conjugated macrocycles: synthesis, morphology and electrochemical characterization

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,7375-7380
DOI: 10.1039/C4OB01043D, PaperAnjan Bedi, Sanjio S. Zade
A 7,8-didodecyloxybenzo[1,2-b:4,3-b[prime or minute]]dithiophene (BdT-Dod) containing a macrocycle was constructed from a thiophene capped BdT-Dod comonomer through a Ti(IV) mediated McMurry reaction. The macrocycle exhibited self-aggregation in the solid state to form microfibers of a thickness of [similar]400 nm.
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Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation

7 September, 2014 - 22:54

Org. Biomol. Chem., 2014, 12,7355-7365
DOI: 10.1039/C4OB00735B, PaperJan-Hendrik Lamm, Johanna Glatthor, Jan-Henrik Weddeling, Andreas Mix, Jasmin Chmiel, Beate Neumann, Hans-Georg Stammler, Norbert W. Mitzel
A series of 1,5-, 1,8-, 9,10- and 1,8,10-alkynyl-substituted anthracenes have been synthesised. Amongst others, 9,10-bis[(trimethylsilyl)ethynyl]anthracene was photo-dimerised. The photodimer is thermally unstable as was investigated by VT NMR spectroscopy.
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