Creating complexity
Chemical synthesis inspires chemists from many different backgrounds, and these scientists are unified in their desire to create and develop methods which enable the creation of complex target molecules from readily available starting materials. The numerous paradigm-shifts which have taken place throughout the history of synthesis have been driven largely by a single impulse: the fascination of building sophistication from simplicity – in other words, creating complexity. This Thematic Series brings together a select group of contributors, recognised for their contributions in the areas of catalysis, radical chemistry, stereoselective synthesis and molecular diversity.
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- Published 24 Jan 2013
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Scheme 1: (A) Silyl glyoxylates as versatile reagents for three-component coupling reactions: representative ...
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Scheme 2: Potential applications of silyl glyoxylate couplings and precedent synthetic intermediates toward t...
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Scheme 3: Three-component coupling with a vinyl nucleophile and elaboration to Ichihara’s aldehyde.
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Scheme 4: Modified Julia olefination as a step-efficient alternative endgame strategy.
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Scheme 5: Three-component coupling with an allyl nucleophile and demonstration of successful ruthenium-cataly...
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Scheme 6: Approaches considered to address the stereochemical issue.
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Scheme 7: Use of a dithiane moiety to excert stereochemical control in the three-component coupling reaction ...
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Scheme 8: Synthesis of a vinyl iodide for nucleophile generation and its use in a three-component coupling re...
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- Review
- Published 18 Mar 2013
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Scheme 1: Key radical step in the total synthesis of (–)-dendrobine.
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Scheme 2: Radical cascade in the total synthesis of (±)-13-deoxyserratine (ACCN = 1,1'-azobis(cyclohexanecarb...
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Scheme 3: Formation of the complete skeleton of (±)-fortucine.
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Scheme 4: Model radical sequence for the synthesis of quadrone.
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Scheme 5: Radical cascade using the Barton decarboxylation.
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Scheme 6: Simplified mechanism for the xanthate addition to alkenes.
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Scheme 7: Synthesis of β-lactam derivatives.
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Scheme 8: Sequential additions to three different alkenes (PhthN = phthalimido).
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Scheme 9: Key cascade in the total synthesis of (±)-matrine (43).
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Scheme 10: Synthesis of complex tetralones.
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Scheme 11: Synthesis of functionalised azaindoline and indole derivatives.
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Scheme 12: Synthesis of thiochromanones.
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Scheme 13: Synthesis of complex benzothiepinones. Conditions: 1) CF3COOH; 2) RCHO / AcOH (PMB = p-methoxybenzy...
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Scheme 14: Formation and capture of a cyclic nitrone.
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Scheme 15: Synthesis of bicyclic cyclobutane motifs.
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Scheme 16: Construction of the CD rings of steroids.
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Scheme 17: Rapid assembly of polyquinanes.
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Scheme 18: Formation of a polycyclic structure via an allene intermediate.
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Scheme 19: A polycyclic structure via the alkylative Birch reduction.
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Scheme 20: Synthesis of polycyclic pyrimidines and indoline structures.
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Scheme 21: Construction of a trans-decalin derivative.
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Scheme 22: Multiple uses of a chloroacetonyl xanthate.
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Scheme 23: A convergent route to spiroketals.
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Scheme 24: A modular approach to 3-arylpiperidines.
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Scheme 25: A convergent route to cyclopentanols and to functional allenes.
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Scheme 26: Allylation and vinylation of a xanthate and an iodide.
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Scheme 27: Vinyl epoxides as allylating agents.
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Scheme 28: Radical allylations using allylic alcohol derivatives.
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Scheme 29: Synthesis of variously substituted lactams.
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Scheme 30: Nickel-mediated synthesis of unsaturated lactams.
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Scheme 31: Total synthesis of (±)-3-demethoxy-erythratidinone.
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Scheme 32: Generation and capture of an iminyl radical from an oxime ester.
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- Full Research Paper
- Published 22 Apr 2013
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Scheme 1: Illustrative examples of a synthetic approach to natural-product-like molecules with over eighty mo...
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Scheme 2: Overview of the proposed synthetic approach. FDIPES = diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10...
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Figure 1: Structures of building blocks used in this study. Panel A: fluorous-tagged initiating building bloc...
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Scheme 3: Synthesis of the initiating building blocks 6a and 6b. TBD = 1,5,7-triazabicyclo[4.4.0]dec-5-ene.
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Scheme 4: Synthesis of the initiating building block 7.
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Scheme 5: Fate of the metathesis reaction of the substrate 32.
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- Published 17 May 2013
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Figure 1: General approach for the use of dendritic catalysts in a dialysis bag.
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Scheme 1: Synthesis of water-soluble iridium catalyst 3.
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Scheme 2: Synthesis of the desymmetrized bipyridine 8.
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Scheme 3: Attachment of the adapted ligand 8 to the dendrimers via a multi-isocyanate coupling, followed by i...
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Scheme 4: Catalytic reductive amination of valine (18) via unfavorable equilibrium reactions in water.
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Figure 2: Formation of 19 catalyzed by the three iridium catalysts.
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Figure 3: Reaction setup to perform compartmentalized catalysis.
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Figure 4: G3 catalyst 16 activity in dialysis device.
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Figure 5: G4 catalyst 17 activity in subsequent runs.
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- Full Research Paper
- Published 03 Jul 2013
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Scheme 1: Formation of (Z)-chloro-exo-methyleneketals.
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Scheme 2: Mechanism of formation of (Z)-chloro-exo-methylenetetrahydrofurans.
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Scheme 3: Stepwise formation of (Z)-chloro-exo-methylenetetrahydrofurans.
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Scheme 4: Optimized protocols to form (Z)-chloro-exo-methylenetetrahydrofurans.
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Scheme 5: Hydration of (Z)-chloro-exo-methylenetetrahydrofurans.
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Scheme 6: Formation of dioxanes.
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Figure 1: X-ray diffraction analysis of dioxanes 35 and 36.
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Scheme 7: Formation of a new spirocyclic dimer.
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Scheme 8: Mechanism leading to dioxanes and spirocycles.
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Scheme 9: (S,S)-syn and (S,R)-syn approaches.
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Scheme 10: Formation of a bridged dimer and a triene.
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Figure 2: X-ray diffraction analysis of two new dimers.
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Scheme 11: Mechanism leading to bridged and dienic dimers.
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