Synthesis of functionalized 1-azaspirocyclic cyclopentanones using bronsted acid or N-bromosuccinimide promoted ring expansions.

No abstract is available for this paper.

• Publication year

  2004

• Venue

  Journal of Organic Chemistry

• Publication date

  2004-07-21

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JO0493572PMID 15307738
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Stereoselective synthesis of (-)-cephalotaxine and C-7 alkylated analogues.

  2004cited by this paper
• New stereoselective entry to azaspirocyclic nucleus of halichlorine and pinnaic acids by radical translocation/cyclization reaction.

  2003cited by this paper
• A flexible approach toward trisubstituted piperidines and indolizidines: synthesis of 6-epi-indolizidine 223A.

  2003cited by this paper
• Total synthesis of (+)-asteltoxin.

  2003cited by this paper
• Strategic use of pinacol-terminated Prins cyclizations in target-oriented total synthesis.

  2003cited by this paper
• Efficient synthesis of the azaspirocyclic core structure of halichlorine and pinnaic acid by intramolecular acylnitroso ene reaction.

  2003cited by this paper
• Lepadiformine: a case study of the value of total synthesis in natural product structure elucidation.

  2003cited by this paper
• Enantiomerically pure cyclobutane derivatives and their use in organic synthesis.

  2003cited by this paper
• A formal construction of fasicularin.

  2003cited by this paper
• The application of cyclobutane derivatives in organic synthesis.

  2003cited by this paper
• Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.

  2003cited by this paper
• Synthesis of alkaloid 223A and a structural revision.

  2002cited by this paper
• Synthesis of alpha-acyl-functionalized azacycles by Pd-catalyzed cross-coupling reactions of alpha-alkoxyboronates with lactam-derived vinyl triflates.

  2002cited by this paper
• Electroauxiliary-assisted sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen: application to the synthesis of spiro compounds.

  2002cited by this paper
• Total synthesis of (+/-)fasicularin via a 2-amidoacrolein cycloaddition.

  2002cited by this paper
• Apoptosis-inducing activity of synthetic intermediates of halichlorine.

  2002cited by this paper
• Ring strain and its effect on the rate of the general-base catalyzed enolization of cyclobutanone.

  2002cited by this paper
• A formal total synthesis of (+/-)-cephalotaxine using sequential N-acyliminium ion reactions.

  2002cited by this paper
• A new total synthesis of the marine tunicate alkaloid lepadiformine.

  2001cited by this paper
• Total synthesis of (+/-)-lepadiformine via an amidoacrolein cycloaddition.

  2001cited by this paper
• Construction of azaspirocyclic ketones through alpha-hydroxyiminium ion or alpha-siloxy epoxide semipinacol rearrangements.

  2001cited by this paper
• 1-Oxaspiro[4.4]nonan-6-ones. Synthetic access via oxonium ion technology, optical resolution, and conversion into enantiopure spirocyclic alpha,beta-butenolides.

  2001cited by this paper
• Suzuki reaction of vinyl triflates from six- and seven-membered N-alkoxycarbonyl lactams with boronic acids and esters.

  2001cited by this paper
• Synthesis of two conformationally constrained analogues of the minor tobacco alkaloid anabasine.

  2000cited by this paper
• An imine addition/ring-closing metathesis approach to the spirocyclic core of halichlorine and pinnaic acid.

  2000cited by this paper
• New oxidative transformations of phenolic and indolic oxazolines: an avenue to useful azaspirocyclic building blocks.

  2000cited by this paper
• Total synthesis of (+/-)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides.

  2000cited by this paper
• Synthesis and Further Reactivity of Functionalized Lactam-Derived Enol Triflates.

  1997cited by this paper
• Amino ketone rearrangements. VI. Synthesis of 2-alkylamino-2-phenylcyclohexanones.

  1966cited by this paper

• Access to Methylidene-Azaspiro[4.5]decatrienones via Radical-Promoted Domino Thio-Functionalization/Dearomative Ipso-Annulation.

  2025cites this paper
• Hypervalent Fluoro-iodane-Triggered Semipinacol Rearrangements: Synthesis of α-Fluoro Ketones.

  2023cites this paper
• Construction of the tetracyclic core of the Lycopodium alkaloid annotinolide C

  2021cites this paper
• Ruthenium(II)-catalyzed amide directed spiroannulation with naphthoquinones: access to spiro-isoindolinone frameworks.

  2020cites this paper
• Recent advances in the ring expansion of cyclobutanols, oxetanols, and azetidinols

  2020cites this paper
• 2-Methyltetrahydrofuran as a Solvent of Choice for Spontaneous Metathesis/Isomerization Sequence

  2019cites this paper
• Deciphering the exceptional selectivity of semipinacol rearrangements in cis-fused β-lactam diols using high-level quantum chemical methods

  2019cites this paper
• Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones.

  2018cites this paper
• Catalyst-free tandem halogenation/semipinacol rearrangement of allyl alcohols with sodium halide in water

  2018cites this paper
• Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols.

  2018cites this paper
• Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones.

  2018cites this paper
• Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP.

  2017cites this paper
• DABCO tribromide immobilized on magnetic nanoparticle as a recyclable catalyst for the chemoselective oxidation of sulfide using H2O2 under metal- and solvent-free conditions

  2014cites this paper
• N-tosyl-3-azacyclohexyne. Synthesis and chemistry of a strained cyclic ynamide.

  2014cites this paper
• Enantioselective total synthesis of pinnaic acid and halichlorine.

  2014cites this paper
• Formal synthesis of (-)-cephalotaxine based on a tandem hydroamination/semipinacol rearrangement reaction.

  2012cites this paper
• 1,3-Dipolar cycloaddition of nitrile imines with α,β-unsaturated lactones, thiolactones and lactams: synthesis of ring-fused pyrazoles

  2012cites this paper
• Organocatalytic asymmetric fluorination/semipinacol rearrangement: an efficient approach to chiral β-fluoroketones.

  2012cites this paper
• Ring expansion of cyclobutylmethylcarbenium ions to cyclopentane or cyclopentene derivatives and metal-promoted analogous rearrangements.

  2011cites this paper
• Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

  2011cites this paper
• Organocatalytic asymmetric halogenation/semipinacol rearrangement: highly efficient synthesis of chiral α-oxa-quaternary β-haloketones.

  2011cites this paper
• Recent Progress in the Use of N-Halo Compounds in Organic Synthesis

  2011cites this paper
• Semipinacol rearrangement in natural product synthesis.

  2011cites this paper
• Carbonylative Palladium-Catalyzed Reactions of Lactam-, Lactone-, and Thiolactone-Derived Vinyl Triflates and Phosphates for the Synthesis of N-, O-, and S-Heterocycles

  2010cites this paper
• Recent progress in the application of N-halo reagents in the synthesis of heterocyclic compounds

  2010cites this paper
• Enamides and enesulfonamides as nucleophiles: formation of complex ring systems through a platinum(II)-catalyzed addition/Friedel-Crafts pathway.

  2009cites this paper
• SYNTHESIS AND APPLICATIONS OF CROSS-LINKED POLY(N-BROMOMALEIMIDE) IN OXIDATION OF VARIOUS ORGANIC COMPOUNDS

  2009cites this paper
• Stereoselective Synthesis of (2S,4R)-4-Hydroxypipecolic Acid

  2008cites this paper
• Synthetic studies toward halichlorine: complex azaspirocycle formation with use of an NBS-promoted semipinacol reaction.

  2008cites this paper
• Activation of sp3 C-H bonds with cobalt(I): catalytic synthesis of enamines.

  2008cites this paper
• Carbonylative Suzuki–Miyaura Coupling Reaction of Lactam‐, Lactone‐, and Thiolactone‐Derived Enol Triflates for the Synthesis of Unsymmetrical Dienones

  2007cites this paper
• The diastereoselective synthesis of functionalised spirocyclic lactams and lactones using a Cope elimination/intramolecular nitrone cycloaddition strategy

  2007cites this paper
• Application of N-halo reagents in organic synthesis

  2007cites this paper
• Recent Approaches to the Construction of 1-Azaspiro[4.5]decanes and Related 1-Azaspirocycles

  2006cites this paper
• Studies on total synthesis of the cylindricine/fasicularin/lepadiformine family of tricyclic marine alkaloids.

  2006cites this paper
• An asymmetric formal synthesis of fasicularin.

  2005cites this paper
• Synthesis of a spirocyclic amine related to the marine natural products halichlorine and pinnaic acid

  2005cites this paper
• Preparation and Suzuki-Miyaura coupling reactions of tetrahydropyridine-2-boronic acid pinacol esters.

  2005cites this paper
• Synthetic chemistry of halichlorine and the pinnaic acids.

  2005cites this paper
• Diasteroselective synthesis of new spiropiperidine scaffolds from the CN(R,S) building block.

  2005cites this paper
• A concise route to the azaspirodecane moiety of halichlorine and structurally related alkaloids.

  2005cites this paper
• Synthesis of Functionalized 1-Azaspirocyclic Cyclopentanones Using Broensted Acid or N-Bromosuccinimide Promoted Ring Expansions.

  2004cites this paper