Still–Gennari Olefination and its Applications in Organic Synthesis

  title={Still–Gennari Olefination and its Applications in Organic Synthesis},
  author={Ignacy Janicki and Piotr Kiełbasiński},
  journal={Advanced Synthesis \& Catalysis},
9 Citations
Silylpyrrole Oxidation En Route to Saxitoxin Congeners Including 11-Saxitoxinethanoic Acid.
Nucleophilic addition to 26 makes possible the preparation of unnatural C11-substituted STXs, and Olefination of this ketone is also demonstrated and, when followed by a redox-neutral isomerization reaction, affords 11-SEA.
Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner-Wadsworth-Emmons (HWE) Olefination.
The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.
A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still–Gennari Type Phosphonates
An improved, straightforward, purification-free procedure for the synthesis of Z-Selective Still–Gennari and Ando modifications of the typically E-selective Horner–Wadsworth–Emmons reaction is presented and a novel Still–gennari type reagent is presented, which may exhibit improved Z-selectivity in Still– Gennari olefinations.
Enantioselective Michael addition to vinyl phosphonates via hydrogen bond-enhanced halogen bond catalysis†
An asymmetric Michael addition of malononitrile to vinyl phosphonates was accomplished by hydrogen bond-enhanced bifunctional halogen bond (XB) catalysis, the first example of the use of XBs for the activation of organophosphorus compounds in synthesis.
Applications of the Horner–Wadsworth–Emmons Olefination in Modern Natural Product Synthesis
The Horner–Wadsworth–Emmons (HWE) reaction is one of the most reliable olefination reaction and can be broadly applied in organic chemistry and natural product synthesis with excellent selectivity.
Synthesis of enantioenriched α-heteroatom functionalised aldehydes by chiral organocatalysis and their synthetic applications
Asymmetric organocatalysis is a versatile method for the enantioselective α-functionalisation of aldehydes. The synthetic scope for chiral α-heteroatom substituted aldehydes is examined including
Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
A palladium‐catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported, exploiting a phosphonate group as an acceptor moiety on the cyclopropane to form a range of substituted benzoxepins.


Identification of a unique resorcylic acid lactone derivative that targets both lymphangiogenesis and angiogenesis.
17, a potent dual V EGFR3 and VEGFR2 inhibitor, effectively suppresses both lymphangiogenesis and angiogenesis in a 3D-microfluidic tumor lymphangIogenesis assay and in vivo corneal assay while SAR131675 blocks only lymphang iogenesis.
Stereochemical Determination of Tuscolid/Tuscorons and Total Synthesis of Tuscoron D and E: Insights into the Tuscolid/Tuscoron Rearrangement.
This study enables detailed insights into the chemically unprecedented tuscolid/tuscoron rearrangement cascade.
Total Synthesis of (±)-Marsupellins A and B via Acetoxymarsupellone Using an Intramolecular Reductive Cyclization of Epoxycyanohydrin Derivative with Cp2TiI.
This unique core common to C3- and C9-oxidized ent-longipinane-type sesquiterpenoids was constructed via a new intramolecular reductive cyclization reaction of an epoxycyanohydrin derivative using Cp2TiI.
New Reaction Mode of the Horner-Wadsworth-Emmons Reaction for the Preparation of α-Fluoro-α,β-unsaturated Esters
Excellent E-selectivity was observed in the Horner-Wadsworth-Emmons (HWE) reactions of ethyl 2-fluoro-2-diethylphosphonoacetate 1 with alkyl aryl ketones 2a-f using Sn(OSO2CF3)2 and
Grubbs' RCM in the Total Synthesis of the Microtubule Stabilizing Drug Laulimalide
Two independent syntheses of the microtubule stabilizing antitumor agent laulimalide are described, which mainly differ with respect to the macrocyclization step. The first synthesis employs a