Continuous flow nitration in miniaturized devices

• Amol A. Kulkarni

Beilstein J. Org. Chem. 2014, 10, 405–424, doi:10.3762/bjoc.10.38

• more of these limitations are experienced in every batch operation it is necessary to check their feasibility for continuous flow processing. Such transformations from batch to flow have been carried out for a lot of reactions and many continuous nitration plants of commercial scale exist. However, the

Convergent synthesis of a tetrasaccharide repeating unit of the O-specific polysaccharide from the cell wall lipopolysaccharide of Azospirillum brasilense strain Sp7

• Pintu Kumar Mandal,
• Debashis Dhara and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2014, 10, 293–299, doi:10.3762/bjoc.10.26

• be among the most promising ones [1]. Azospirillum brasilense (A. brasilense) is a plant growth-promoting bacterium, found abundant in the rizosphere of several leguminous plants and regular crops such as wheat, rice, corn etc. Azospirillum is a Gram-negative rizobacterium, which exerts a variety of

• Azospirillum against crown gall disease in plants [8][9], leaf and/or vascular diseases of tomato [10][11] as well as inhibitory properties against the development of bacterial diseases or promoting disease resistance on rice crops [12]. It has been demonstrated that Azospirilla produce a diverse range of

• macromolecules such as exopolysaccharides (EPS), lipopolysaccharides (LPS) and capsular polysaccharides (CPS), which influence their interactions with plants [13][14][15]. There are only a limited number of reports on structural studies of the LPS present in the cell wall of Azospirilla species despite their

Decandrinin, an unprecedented C₉-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra

• Hui Wang,
• Min-Yi Li,
• Félix Zongwe Katele,
• Tirumani Satyanandamurty,
• Jun Wu and
• Gerhard Bringmann

Beilstein J. Org. Chem. 2014, 10, 276–281, doi:10.3762/bjoc.10.23

• have been reported from plants of the genera Abies, Cephalotaxus, Colus, Cordia, Hyptis, Isodon, Pinus, Premna, Salvia, Taiwania, Thuja, and Vitex, including a 1,2-seco-abietane [8], a 1,10-seco-abietane [9][10], three 2,3-seco-abietanes [8][11][12][13], three 3,4-seco-abietanes [8][14], 31 4,5-seco

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

• Léa Bouché,
• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 213–223, doi:10.3762/bjoc.10.17

• in natural products, in particular as toxins in marine organisms or plants [6][7]. A few reports in the literature deal with seven-membered polyhydroxylated ethers like septanosides (containing an anomeric center) [8] as well as compounds without an acetal moiety. Known methods for the construction

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

• Andivelu Ilangovan and
• Shanmugasundar Saravanakumar

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

• -aminopyrrolidine compounds are synthesised in plants from open-chained bisamides by enzymatic cyclization. It is assumed that both forms of bisamides undergo a cycloaddition reaction with a co-occurring flavanol to form highly bioactive flavaglines [1][2]. For example, odorine (2) acted as a building block for

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• –vis region [25]. CT interactions have been employed to induce the supramolecular interactions between donors and acceptors, and lead to the formation of two-component organogels [26][27][28][29][30]. 18β-Glycyrrhetinic acid (GA, 1), a natural pentacyclic triterpenoid obtained from medicinal plants in

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

• Silke Felix,
• Louis P. Sandjo,
• Till Opatz and
• Gerhard Erkel

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

• promoter and subsequently triggering apoptosis in Colo 320 cells. Drimane sesquiterpenes are widespread in plants, fungi and marine organisms such as algae, sponges and corals and have attracted some attention for their potent antibacterial, antifungal, cytotoxic, antifeedant, phytotoxic, piscicidal and

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

• Tobias A. M. Gulder,
• Snežana Neff,
• Traugott Schüz,
• Tammo Winkler,
• René Gees and
• Bettina Böhlendorf

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

• to be transformed into actively growing cultures again. Coumarins in general constitute a large group of bioactive natural products, mostly isolated from plants. Most of these plant-derived compounds are polyphenols that are often further modified by most diverse functionalization reactions, such as

• ); ESIMS(−) m/z: 693.3 [2M − H]−, 346.2 [M − H]−; ESIMS(+) m/z: 348.2 [M + H]+. Biological testing. Cut leaf disks (15 mm2) of the respective host plants (see below) were placed on water agar in multi-well plates (24-well format) and sprayed with 12 µL aqueous test solution of varying concentrations (dose

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• (117). The aristolactams and aristolochic acids have a broad spectrum of biologically interesting properties. Although both can be isolated from the same plants, their biological activity is highly variable. Herbal drugs containing aristolochic acids display cytotoxic activities and inhibitory effects

• different hetisine alkaloids have been isolated from different species of the plants Aconitum and Delphinium, and to a lesser extend from Rumex, Consolida and Spiraea [167][168]. These plants have been widely used in traditional herbal medicine and further pharmacological studies revealed that hetisine

Chemistry in flow systems III

• Andreas Kirschning

Beilstein J. Org. Chem. 2013, 9, 1696–1697, doi:10.3762/bjoc.9.193

• reactors, mixers and interfaces for the online monitoring of continuous processes. The major inspiration came from the process and development units in the chemical industry, where continuously operated pilot plants already played a key role. Conceptually, highly modular microreaction systems developed by

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• to their renewable, environmentally benign, naturally abundant, biodegradable and biocompatible nature, as well as their excellent mechanical properties and anticipated low cost [24][25][26]. CNCs are obtained from semicrystalline cellulose derived from wood fibers and plants. Potential applications

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

• Serge Lavoie,
• Charles Gauthier,
• Jean Legault,
• Sylvain Mercier,
• Vakhtang Mshvildadze and
• André Pichette

Beilstein J. Org. Chem. 2013, 9, 1333–1339, doi:10.3762/bjoc.9.150

• assessment. The photograph from our graphical abstract is from Robert H. Mohlenbrock @ USDA-NRCS PLANTS Database / USDA NRCS. 1995. Northeast wetland flora: Field office guide to plant species. Northeast National Technical Center, Chester.

Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids

• Matthew T. Richers,
• Chenfei Zhao and
• Daniel Seidel

Beilstein J. Org. Chem. 2013, 9, 1194–1201, doi:10.3762/bjoc.9.135

• ; quinazoline alkaloid; Introduction Quinazoline alkaloids are a class of naturally occurring compounds with a range of medicinal properties and have been indicated for use as bronchodilators, vasodilators, anti-inflammatory agents and acetylcholinesterase inhibitors [1][2][3][4][5]. Many of the plants these

Caryolene-forming carbocation rearrangements

• Quynh Nhu N. Nguyen and
• Dean J. Tantillo

Beilstein J. Org. Chem. 2013, 9, 323–331, doi:10.3762/bjoc.9.37

• , Streptomyces bacteria, Sinacalia tangutica plants, and Eurypon sponges (Figure 1) [3][4][5][6]. The carbon skeleton of 1 is unusual, not only because it contains concatenated 4-, 6-, and 7-membered rings, but also in that it bears a bridgehead double bond. As noted in the original isolation report [2], this

Flow photochemistry: Old light through new windows

• Jonathan P. Knowles,
• Luke D. Elliott and
• Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

• Nylon 6, proceeds by irradiation of cyclohexane with NOCl and HCl, and is carried out in dedicated plants producing >100,000 tons per annum. Conventional techniques & equipment For well over half a century the most dependable apparatus for laboratory scale organic photochemistry has been the immersion

Tricyclic flavonoids with 1,3-dithiolium substructure

• Lucian G. Bahrin,
• Peter G. Jones and
• Henning Hopf

Beilstein J. Org. Chem. 2012, 8, 1999–2003, doi:10.3762/bjoc.8.226

• ; dithiolium salts; flavonoids; Introduction The great diversity in physical, chemical and biochemical properties of flavonoids gives them the ability to influence the biological activity of plants, microbes and animals [1][2][3]. Flavonoids are known to be good antioxidants and this is believed to be the

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• monoterpenes de novo [33] but they are also able to sequester glycosidically bound terpene precursors from their food plants [51][52][53] which is highly interesting with regards to the evolution of insect-plant relationships and insect defense chemistry. At present, nothing is known about the formation of

• Alloxysta victrix. For the identification of compounds other than Y and Z see [1]. Structures of iridoids from insects and plants. Absolute configurations of 19 and 20 are "educated guesses". Biosynthetic ways to iridoids from geraniol. Synthesis of the trans-fused iridomyrmecins A and B. Reaction

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

• Nicole Zimmermann,
• Robert Hilgraf,
• Lutz Lehmann,
• Daniel Ibarra and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140

• synthesis; trans-fused dihydronepetalactone; Introduction The endohyperparasitoid wasp Alloxysta victrix is part of the tetratrophic system of oat plants (Avena sativa), grain aphids (Sitobion avenae), primary parasitoids (Aphidius uzbekistanicus) and hyperparasitoids (Alloxysta victrix). Chemical

Antibiotic and cytotoxic peptides

• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1144–1145, doi:10.3762/bjoc.8.127

• : chemical compounds that provide the producing species with specific protective mechanisms or other advantages. Among these, there are, e.g., peptides that display antibiotic/antimicrobial activity. These have been isolated from plants, invertebrates, vertebrates, and humans, but also from microorganisms

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

• Dieter Enders,
• Jeanne Fronert,
• Tom Bisschops and
• Florian Boeck

Beilstein J. Org. Chem. 2012, 8, 1112–1117, doi:10.3762/bjoc.8.123

• reaction; asymmetric synthesis; organocatalysis; proline; smyrindiol; Introduction Furocoumarins are a group of compounds that are structurally derived from psoralen or angelicin (Figure 1) [1]. Naturally occurring furocoumarins are mainly found in plants of the Apiaceae and Rutaceae families [2] and are

Phytoalexins of the Pyrinae: Biphenyls and dibenzofurans

• Cornelia Chizzali and
• Ludger Beerhues

Beilstein J. Org. Chem. 2012, 8, 613–620, doi:10.3762/bjoc.8.68

• ) accumulated in Pyrinae plants after either natural infection or artificial inoculation [3][4][5][6][7][8][9][13][14][15][16][17][18][19][21]. A single publication reports biphenyl and dibenzofuran formation in response to bacterial challenge [12]. Inoculation of an apple cultivar with the fire-blight-causing

• biphenyls and dibenzofurans were detected in intact plants of the Pyrinae; however, cell cultures of an apple cultivar accumulated the biphenyl derivative 2'-glucosyloxyaucuparin (7) and the dibenzofuran glucoside malusfuran (20) [10][11]. The most widely distributed biphenyl is aucuparin (3), which was

• dibenzofurans was observed in elicitor-treated cell cultures of a scab-resistant apple cultivar, which formed the biphenyls aucuparin (3), 2'-hydroxyaucuparin (6), and 2'-glucosyloxyaucuparin (7) in addition to the dibenzofuran malusfuran (20) [10][11]. For intact plants, co-occurrence of the two classes of

Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

• Teresa Weise,
• Marco Kai,
• Anja Gummesson,
• Armin Troeger,
• Stephan von Reuß,
• Silvia Piepenborn,
• Francine Kosterka,
• Martin Sklorz,
• Ralf Zimmermann,
• Wittko Francke and
• Birgit Piechulla

Beilstein J. Org. Chem. 2012, 8, 579–596, doi:10.3762/bjoc.8.65

• organisms such as invertebrates, plants and fungi. As a first step to study volatile-based bacterial–plant interactions, the emission profile of Xanthomonas c. pv. vesicatoria 85-10 was determined by using GC/MS and PTR–MS techniques. More than 50 compounds were emitted by this species, the majority

• which bacterial effector proteins enter the plant cells to interfere with cellular processes, to the benefit of the bacterium [11]. However, some plants react to the effector proteins by local cell death, a hypersensitive response, and are able to escape bacterial spreading and invasion. Apart from

• field of interest emerged, when it became apparent that also bacteria emit a plethora of volatiles, which may influence other organisms, such as invertebrates, plants and fungi [20][21]. There is increasing information about those volatiles emitted by bacteria, especially rhizobacteria, e.g., [22][23

The volatiles of pathogenic and nonpathogenic mycobacteria and related bacteria

• Thorben Nawrath,
• Georgies F. Mgode,
• Bart Weetjens,
• Stefan H. E. Kaufmann and
• Stefan Schulz

Beilstein J. Org. Chem. 2012, 8, 290–299, doi:10.3762/bjoc.8.31

• is a known volatile from several plants [29], and the endophytic fungus Muscodor albus [30]. The structure of 19 has recently been revised [29]. This compound may act as marker for norcardiae, as it was produced as a single compound by Nocardia spp. grown on a 7H11 medium and has so far not been

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• of bacterial cell membranes can be tuned, e.g., by the introduction of methyl branches or olefinic double bonds [1]. The biosynthesis of FAs is a repetitive chain elongation process catalysed in animals and fungi by multifunctional megasynthases, and in plants or bacteria by a set of discrete enzymes

Biosynthesis and function of secondary metabolites

• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2011, 7, 1620–1621, doi:10.3762/bjoc.7.190

• poses severe clinical problems in the treatment of infectious diseases. This Thematic Series on the biosynthesis and function of secondary metabolites deals with the discovery of new biologically active compounds from all kinds of sources, including plants, bacteria, and fungi, and also with their