Chemical synthesis articles within Nature Chemistry

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  • News & Views |

    Pattern mapping is a synthetic tactic that is complementary to standard retrosynthetic analysis. When combined with the concept of traceless stereochemical guidance, it leads to an efficient synthesis of the steroidal natural product (±)-aplykurodinone-1.

    • Nathan Collett
    •  & Rich G. Carter

  • News & Views |

    A versatile intermediate has been shown to provide access to a wide variety of compounds in the cortistatin family. This approach offers the most efficient total synthesis of the cortistatins reported so far.

    • Richmond Sarpong

  • Article |

    The cortistatins have attracted a lot of attention in the synthetic community because of their interesting biological activity. Here, four of the cortistatin family are prepared from a common precursor. This efficient synthesis will assist in an investigation of structure–activity relationships and understanding of the biosynthetic route to these compounds.

    • Alec N. Flyer
    • , Chong Si
    •  & Andrew G. Myers

  • Research Highlights |

    A sugar-derived amphiphilic molecule has been prepared that immobilizes oil into a solid from a mixture with water and enables its subsequent recovery.

    • Anne Pichon

  • News & Views |

    Interlocking molecules in solution usually requires recognition motifs that direct the assembly of the building blocks. Triply interlocked catenanes have now been constructed just relying on the interpenetration of structures typical of the solid state and slow reversible covalent bond formation.

    • Jonathan E. Beves
    •  & David A. Leigh

  • Article |

    Interlocked molecules commonly include one (or more) monocyclic component — examples comprising bicyclic or tricyclic structures are much more rare and usually involve metal–ligand coordination or additional templates. Now, the dynamic self-assembly of twenty organic molecules in a one-pot synthesis has been shown to produce tetrahedral covalent cages, which interpenetrate during the process to form triply interlocked dimers.

    • Tom Hasell
    • , Xiaofeng Wu
    •  & Andrew I. Cooper

  • Article |

    A Lewis-acid-catalysed 1,3-dipolar cycloaddition provides rapid access to a variety of substituted spirooxindoles. Initial cellular evaluations supports the view that compound collections based on natural-product-inspired scaffolds constructed with complex stereochemistry, and decorated with assorted substituents, will be a rich source of compounds with diverse bioactivity.

    • Andrey P. Antonchick
    • , Claas Gerding-Reimers
    •  & Herbert Waldmann

  • News & Views |

    The plant-derived sesquiterpene englerin A is a potent inhibitor of several renal cancer cell lines. Two recent total syntheses have utilized cationic gold(I)-complexes to coax readily available open-chain precursors into englerin's challenging oxotricyclic core with enzyme-like precision.

    • Matthieu Willot
    •  & Mathias Christmann

  • Article |

    Nitric oxide, NO, has an unpaired electron and is widely used and studied in such diverse fields as biochemistry and atmospheric chemistry. Its radical nature means that singly charged species are common, but now two electrons have been added to give a radical dianion in an yttrium complex.

    • William J. Evans
    • , Ming Fang
    •  & Jeffrey I. Zink

  • Research Highlights |

    A peptide-catalysed bromination provides access to an important class of chiral compounds in high enantiomeric purity.

    • Stephen Davey

  • Perspective |

    Sunlight is potentially an ideal green 'reagent' for chemical synthesis, but poor absorption by organic substrates makes direct solar photochemistry generally inefficient. Here, recent progress in the use of the simple organometallic complexes to harness the power of the sun is summarized, and prospects for the future of this exciting field highlighted.

    • Tehshik P. Yoon
    • , Michael A. Ischay
    •  & Juana Du

  • Article |

    Metal-containing fullerene cages are widely known, but hard to characterize because of their reactivity towards empty cages. Now the molecular and crystal structures of lithium-containing C60 molecules have been determined.

    • Shinobu Aoyagi
    • , Eiji Nishibori
    •  & Hiromi Tobita

  • Article |

    Covalent organic frameworks (COFs) organize organic subunits into predictable and precise networks with long-range order. The limited generality of methods for COF synthesis has thus far precluded the incorporation of complex building blocks into these emerging materials. Now, a new Lewis acid-catalysed protocol for boronic ester formation provides a two-dimensional COF containing stacked phthalocyanine chromophores.

    • Eric L. Spitler
    •  & William R. Dichtel

  • Article |

    Freeze-drying of aqueous myoglobin–polymer surfactant nanoconjugates affords a water-free solid that melts at room temperature to produce a viscous solventless liquid protein that exhibits near-native secondary structure and reversible dioxygen binding. The results challenge the accepted role of solvent molecules in mediating protein structure and function, and offer new opportunities in protein-based nanoscience and bionanotechnology.

    • Adam W. Perriman
    • , Alex P. S. Brogan
    •  & Stephen Mann

  • Article |

    The development of benign methods for carbon–carbon bond formation is a continuing challenge. Here, a simple procedure for the hydroacylation of α,β-unsaturated esters is described, in which auto-oxidation of aldehydes and subsequent acyl radical addition to α,β-unsaturated esters occurs without the need for additional reagents.

    • Vijay Chudasama
    • , Richard J. Fitzmaurice
    •  & Stephen Caddick

  • News & Views |

    Despite knowing that the active centres of many metalloprotein enzymes are iron porphyrin 'haem' complexes, chemists find them difficult to imitate. Now, the assembly of haem-like centres into a crystalline, stable, nanoporous array shows promise for biomimetic catalysis.

    • Joseph T. Hupp

  • Article |

    Converting dioxygen into more reactive species is extremely useful for direct oxygenation of organic compounds, but doing this with cheap and non-polluting elements is difficult. Now, a carbene-activated silylene has been shown to activate dioxygen, resulting in the isolation of elusive silicon–oxygen species at room temperature.

    • Yun Xiong
    • , Shenglai Yao
    •  & Matthias Driess

  • Article |

    A convergent route to stereodefined skipped polyenes, which proceeds through the direct union of vinylcyclopropanes with alkynes, is described. Overall, C?C bond formation occurs in concert with the establishment of up to three stereodefined alkenes, through a tandem stereoselective metallacycle-mediated coupling/stereospecific fragmentation sequence.

    • Todd K. Macklin
    •  & Glenn C. Micalizio

  • Article |

    Optically driven phase transitions are widely used in optical memory devices, and the materials showing this effect are normally chalcogenides or organic compounds. Now a room-temperature light-induced phase transition between metal and semiconducting phases has been observed in a titanium oxide material.

    • Shin-ichi Ohkoshi
    • , Yoshihide Tsunobuchi
    •  & Hiroko Tokoro

  • Article |

    The difficulty in the stereoselective introduction of 1,2-cis-glycosides is a major stumbling block in the solid-supported synthesis of oligosaccharides. Now, this has been achieved for a biologically important glucoside containing multiple 1,2-cis-glycosidic linkages with complete anomeric control by using glycosyl donors having a participating (S)-(phenylthiomethyl)benzyl chiral auxiliary at C-2.

    • Thomas J. Boltje
    • , Jin-Hwan Kim
    •  & Geert-Jan Boons

  • Article |

    The composition of a dynamic combinatorial library can be altered by adding a target molecule that either stabilizes (or destabilizes) one or more of its members. The range of reversible chemical reactions compatible with biological targets such as proteins is somewhat limited, but now it has been shown that aniline-catalysed acylhydrazone formation is effective in this context.

    • Venugopal T. Bhat
    • , Anne M. Caniard
    •  & Michael F. Greaney

  • Article |

    Iron is an abundant, low cost and environmentally benign metal. Here, iron complexes are shown to be the most effective catalysts for asymmetric O–H insertion reactions. These results should encourage the use of iron, rather than more traditional precious metals, in the development of greener organometallic catalysts for asymmetric transformations.

    • Shou-Fei Zhu
    • , Yan Cai
    •  & Qi-Lin Zhou

  • Article |

    The ability to selectively transform the C–H bonds of simple alkanes to useful functional groups such as alcohols is a key step in the move away from petrochemical feedstocks. Now, it has been shown that the oxidation of alkanes can be catalysed by a bulky polyoxometalate species using hydrogen peroxide as a stoichiometric oxidant.

    • Keigo Kamata
    • , Kazuhiro Yonehara
    •  & Noritaka Mizuno

  • Research Highlights |

    Two different but successful approaches to the synthesis of (+)-complanadine A will help in investigations of its interesting biological activity.

    • Stephen Davey

  • Review Article |

    The synthesis or separation of chiral compounds is crucial for many areas of chemistry, with chiral solids having important roles as catalysts or separating agents. This Review covers recent progress and future avenues for developing methods of preparing chiral solids from achiral starting materials.

    • Russell E. Morris
    •  & Xianhui Bu

  • Article |

    Porous coordination polymers — PCPs, also known as metal–organic framework materials — have been widely investigated for their useful properties, but controlling their size and shape in a nanocrystalline form is difficult. Now, a rapid method of preparing porous crystalline nanosized PCPs that uses a microemulsion system under ultrasonic irradiation has been reported.

    • Daisuke Tanaka
    • , Artur Henke
    •  & Juergen Groll

  • Research Highlights |

    A double-reductive alkylation of amides with two different organometallic compounds allows the direct formation of a tertiary alkylamines in one pot.

    • Stephen Davey

  • News & Views |

    The convergent total synthesis of the pore-forming polytheonamide B — a linear peptide natural product — pokes holes through perceived limitations in de novo peptide synthesis, and provides access to novel synthetic membrane channels.

    • Craig J. Forsyth

  • News & Views |

    A strong acid catalyst and a small change to one reactant have transformed a 37-year-old 'curiosity' into a useful chemical reaction that has great potential in organic synthesis.

    • Sarah E. Steinhardt
    •  & Christopher D. Vanderwal

  • Article |

    The reactivity of organoaluminium reagents makes them particularly attractive nucleophiles for a wide range of organic reactions. Here, the use of metal halide catalysts provides access to functionalized organoaluminium reagents directly from the metal. The utility of these organoaluminium reagents is then demonstrated by their reaction with a wide variety of electrophilic coupling partners.

    • Tobias Blümke
    • , Yi-Hung Chen
    •  & Paul Knochel

  • Article |

    Chiral thiols and organosulfur compounds are important in many areas of chemistry but there are relatively few methods available for their efficient enantioselective synthesis. Here, a kinetic resolution of chiral thiols is reported along with a demonstration that a concomitant desymmetrization of the acylating agent is beneficial for the selectivity of both processes.

    • Aldo Peschiulli
    • , Barbara Procuranti
    •  & Stephen J. Connon

  • News & Views |

    The long-awaited first total synthesis of the structurally intriguing natural product palau'amine has now been achieved. The synthesis features cascade reactions and an 'across ring' stitching of a 'macropalau'amine', and sets the bar for future efforts towards an enantioselective variant.

    • Daniel Romo

  • Article |

    A triflimide-catalysed rearrangement of N-allylhydrazones has been developed that allows for the generation of a sigma bond between two unfunctionalized sp3 carbons such that no clear marker remains for how the bond was formed. This traceless bond construction offers new avenues for convergent fragment coupling in synthetic strategies.

    • Devon A. Mundal
    • , Christopher T. Avetta Jr
    •  & Regan J. Thomson

  • Review Article |

    The field of organocatalysis has grown rapidly in the past decade to become, along with metal catalysis and biocatalysis, a third pillar of asymmetric catalysis. Here, progress in the use of organocatalytic cascade reactions for total synthesis is reviewed. The elegance and efficiency of such cascades mean that they have emerged as a powerful tool in synthetic organic chemistry.

    • Christoph Grondal
    • , Matthieu Jeanty
    •  & Dieter Enders

  • Article |

    The synthesis of interlocked compounds such as catenanes and rotaxanes has undergone much development in recent years, but molecular knots are still relatively hard to make. It has now been shown that a linear bipyridine oligomer can fold around a single zinc-ion template to form a complex that can be cyclized to give a molecular trefoil knot.

    • Jun Guo
    • , Paul C. Mayers
    •  & Christopher A. Hunter

  • Research Highlights |

    Replacing readily hydrolysable ester linkages with amides in a natural adjuvant has resulted in not only more stable, but significantly more active and less toxic analogues.

    • Georgia Tsoukala

  • News & Views |

    The stereochemical lability of cycloalkylzinc reagents combined with a large difference in reactivity between epimers has been exploited to form a wide variety of interesting organic compounds with both high yields and diastereoselectivities.

    • Frank Glorius

  • News & Views |

    An enzyme that is unusually tolerant of a truly broad range of substrates can catalyse aldol-type chemistry on sugars in which the various hydroxyl groups are protected. The new methodology combines some of the most important advantages of enzyme and small-molecule catalysis.

    • Benjamin G. Davis

  • Article |

    The selective construction of multiple adjacent stereocentres is an important challenge for synthetic organic methodology, and only a handful of catalytic methods exist that can forge adjacent quaternary and tertiary stereocentres. Here, a palladium-catalysed multiple-bond-forming cascade leads to the construction of such systems in high yield, diastereomeric ratio and enantiomeric excess.

    • Jan Streuff
    • , David E. White
    •  & Brian M. Stoltz

  • Article |

    Ready access to sugars in which the various hydroxyl groups are differentially protected will be of benefit in the production of vaccines, antibiotics and drugs. Here, a chemoenzymatic method that provides a direct route to such protected sugars is described.

    • Dennis G. Gillingham
    • , Pierre Stallforth
    •  & Donald Hilvert

  • News & Views |

    Embedding platinum nanoparticles in a polymer matrix produces a system that reacts like a homogeneous catalyst, but provides the stability and separation advantages of a heterogeneous one.

    • Gadi Rothenberg

  • News & Views |

    Synthetic procedures for making nanoparticles often result in samples that contain a range of different particle sizes. By using hollow self-assembled metal–organic spheres as templates, however, it is possible to make silica nanoparticles with uniform shapes and sizes in a precisely controlled fashion.

    • Boris Breiner
    •  & Jonathan R. Nitschke

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