Org. and Biomol. Chem.

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Strategies for desymmetrising trehalose to synthesise trehalose glycolipids

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5558-5562
DOI: 10.1039/C4OB00587B, PerspectiveChia-Hui Wu, Cheng-Chung Wang
The desymmetrisation and regioselective protection of trehalose are major challenges in the chemical synthesis of biologically essential trehalose glycolipids.
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Chemoselective reduction and self-immolation based FRET probes for detecting hydrogen sulfide in solution and in cells

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5629-5633
DOI: 10.1039/C4OB00923A, PaperBifeng Chen, Peng Wang, Qingqing Jin, Xinjing Tang
A general approach in designing H2S fluorescent probes based on FRET and self-immolative linkers.
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Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5601-5610
DOI: 10.1039/C4OB00950A, PaperGangarajula Sudhakar, Shruthi Bayya, Vilas D. Kadam, Jagadeesh Babu Nanubolu
The total syntheses of gonytolide C and related compounds have been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing ketone, followed by the diastereoselective intramolecular cyclization.
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Iron-catalyzed radical aryldifluoromethylation of activated alkenes to difluoromethylated oxindoles

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5582-5585
DOI: 10.1039/C4OB00758A, CommunicationJian-Yong Wang, Xin Zhang, Yan Bao, Yue-Ming Xu, Xiu-Fen Cheng, Xi-Sheng Wang
An iron-catalyzed aryldifluoromethylation of activated alkenes has been developed, which is a rare example where a cosolvent is used to improve the yield along with Fenton's reagent.
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Palladium-catalyzed microwave-assisted direct arylation of imidazo[2,1-b]thiazoles with aryl bromides: synthesis and mechanistic study

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5773-5780
DOI: 10.1039/C4OB00600C, PaperYi-Shuo Zhu, Benyi Shi, Ran Fang, Xiaoxuan Wang, Huanwang Jing
A palladium-catalyzed regioselective C-H arylation of imidazo[2,1-b]thiazoles under microwave irradiation via a concerted metalation-deprotonation (CMD) pathway was developed.
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Elucidating factors leading to acidolytic degradation of sterically strained oligoether dendrons

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5621-5628
DOI: 10.1039/C4OB00540F, PaperJ. Karabline-Kuks, A. Fallek, M. Portnoy
Monitoring of the disassembly of third-generation sterically crowded oligoether dendrons in acidic solution reveals their exact degradation sequence, synergistically induced by electron donation and steric strain.
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Synthesis of functionalized chromones through sequential reactions in aqueous media

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5757-5765
DOI: 10.1039/C4OB00618F, PaperSaber Mehrparvar, Saeed Balalaie, Mahnaz Rabbanizadeh, Frank Rominger, Elmira Ghabraie
An efficient synthesis protocol has been developed for diversity-oriented functionalized compounds via four-component reaction of chromone carbaldehydes, Meldrum's acid, 4-hydroxyl coumarin or 6-methyl-4-hydroxyl-pyrone and primary alcohols in aqueous media.
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Pd(OAc)2/DABCO as an efficient and phosphine-free catalytic system for the synthesis of single and double Weinreb amides by the aminocarbonylation of aryl iodides

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5727-5732
DOI: 10.1039/C4OB00729H, PaperSandip T. Gadge, Bhalchandra M. Bhanage
Single and double Weinreb amides were synthesized using a Pd(OAc)2 catalyst and DABCO as an inexpensive and stable ligand using carbonylation methodology under phosphine-free conditions.
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Electrophilicity and nucleophilicity of commonly used aldehydes

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5781-5788
DOI: 10.1039/C4OB00555D, PaperSanjay Pratihar
The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes.
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Hydroxyl radical induced oxidation of theophylline in water: a kinetic and mechanistic study

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5611-5620
DOI: 10.1039/C4OB00102H, PaperM. M. Sunil Paul, U. K. Aravind, G. Pramod, A. Saha, C. T. Aravindakumar
Evidence is reported for the addition and hydrogen abstraction reactions of hydroxyl radicals with an important pharmaceutically active compound, theophylline.
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Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5578-5581
DOI: 10.1039/C4OB00796D, CommunicationJianbin Chen, Kishore Natte, Anke Spannenberg, Helfried Neumann, Matthias Beller, Xiao-Feng Wu
A convenient and mild procedure for double carbonylation of o-dibromobenzene with various 2-amino pyridines and naturally occurring amines has been developed. N-Substituted phthalimides were produced in good to excellent yields. Furthermore, thalidomide was produced in excellent yield under these conditions.
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Bis-chlorination of a hexapeptide-PCP conjugate by the halogenase involved in vancomycin biosynthesis

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5574-5577
DOI: 10.1039/C4OB00474D, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Patrick C. Schmartz, Katja Zerbe, Khaled Abou-Hadeed, John A. Robinson
The vancomycin biosynthetic halogenase can bis-chlorinate both [small beta]-hydroxytyrosine residues-2 and -6 in a model substrate comprising a PCP-linked hexapeptide.
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An indolocarbazole dimer as a new stereodynamic probe for chiral 1,2-diamines

11 July, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,5464-5468
DOI: 10.1039/C4OB00872C, PaperHae-Geun Jeon, Min Jun Kim, Kyu-Sung Jeong
An indolocarbazole dimer functions as a new stereodynamic probe determining the absolute configurations of chiral 1,2-diamines.
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One-pot native chemical ligation of peptide hydrazides enables total synthesis of modified histones

11 July, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,5435-5441
DOI: 10.1039/C4OB00715H, PaperJiabin Li, Yuanyuan Li, Qiaoqiao He, Yiming Li, Haitao Li, Lei Liu
One of the rising demands in the field of protein chemical synthesis is the development of facile strategies that yield the protein in workable quantities and homogeneity, with fewer handling steps.
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Synthesis and pharmacological evaluation of like- and unlike-configured tetrahydro-2-benzazepines with the [small alpha]-substituted benzyl moiety in the 5-position

9 July, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,5407-5426
DOI: 10.1039/C4OB00510D, PaperPeer Hasebein, Bastian Frehland, Kirstin Lehmkuhl, Roland Frohlich, Dirk Schepmann, Bernhard Wunsch
5-Substituted tetrahydro-2-benzazepines were prepared and the relationship between the structure, in particular the stereochemistry, and the [sigma]1 affinity was analyzed.
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The structure of 3-(diethylborylethynyl)pyridine: a nonplanarly arranged cyclic trimer

9 July, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,5382-5387
DOI: 10.1039/C4OB00849A, PaperShigeharu Wakabayashi, Mitsumi Kuse, Aimi Kida, Seiji Komeda, Kazuyuki Tatsumi, Yoshikazu Sugihara
The cyclic trimer of 3-(diethylborylethynyl)pyridine is conformationally flexible enough to be affected by the crystal packing.
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Electrophilic sulfhydration of 8-nitro-cGMP involves sulfane sulfur

9 July, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,5360-5364
DOI: 10.1039/C4OB00868E, CommunicationV. Terzic, D. Padovani, V. Balland, I. Artaud, E. Galardon
The complex chemistry taking place between the messenger 8-nitro-cGMP and the gaseous transmitter H2S is governed by dioxygen and thiols.
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One-step synthesis of diazaspiro[4.5]decane scaffolds with exocyclic double bonds

9 July, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,5356-5359
DOI: 10.1039/C4OB00516C, CommunicationLidong Li, Qiong Hu, Pingping Zhou, Haifeng Xie, Xiaorong Zhang, Hao Zhang, Yadong Hu, Fei Yin, Yimin Hu
Unactivated yne-en-ynes reacted with a range of substituted aryl halides in the presence of Pd(OAc)2-PPh3 to afford diazaspiro[4.5]decane with exocyclic double bonds.
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Nazarov-like cyclization reactions

9 July, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,5331-5345
DOI: 10.1039/C4OB00804A, Review ArticleMartin J. Di Grandi
This review discusses novel Nazarov cyclization variations and their application to the synthesis of complex molecules.
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Synthesis of 2,3-dihydro-1H-indazoles by Rh(III)-catalyzed C-H cleavage of arylhydrazines

9 July, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,5469-5476
DOI: 10.1039/C4OB00921E, PaperJinzhong Yao, Ruokun Feng, Cong Lin, Zhanxiang Liu, Yuhong Zhang
A rhodium-catalyzed efficient method for the synthesis of 2,3-dihydro 1H-indazoles is described.
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