A cycloaddition-rearrangement approach to the squalestatins

A cycloaddition-rearrangement approach to the squalestatins

Reaction of diazodiketoester 4 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate generates the 6,8- dioxabicyclo[3.2.1]octane 5 as a single regio- and stereo-isomer in good yield. Elaboration provides a suitable alcohol 7 for acid-catalysed rearrangement to give the...

Deskribapen osoa

Xehetasun bibliografikoak
Egile Nagusiak:	Hodgson, D, Bailey, J, Harrison, T
Formatua:	Journal article
Argitaratua:	1996

Antzeko izenburuak

Evolution of a cycloaddition-rearrangement approach to the squalestatins: a quarter-century odyssey
nork: Almohseni, HAA, et al.
Argitaratua: (2020)

Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins
nork: Hodgson, D, et al.
Argitaratua: (2000)

Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
nork: Hodgson, D, et al.
Argitaratua: (2000)

Synthetic studies toward the Zaragozic agios (squalestatins).
nork: Villalonga-Barber, C, et al.
Argitaratua: (2000)

Squarate desymmetrisation–ozonolysis as an approach to β-substituted-α-ketosuccinates and squalestatin synthesis
nork: Sintim, H, et al.
Argitaratua: (2019)

Alkene ozonolysis in the presence of diazo functionality: accessing an intermediate for squalestatin synthesis
nork: Almohseni, HAA, et al.
Argitaratua: (2019)

Catalytic enantioselective rearrangements and cycloadditions involving ylides from diazo compounds
nork: Hodgson, D, et al.
Argitaratua: (2000)

Catalytic enantioselective rearrangements and cycloadditions involving ylides from diazo compounds
nork: Hodgson, D, et al.
Argitaratua: (2001)

Squalestatin alters the intracellular trafficking of a neurotoxic prion peptide
nork: Williams Alun, et al.
Argitaratua: (2007-11-01)

Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling
nork: Fegheh-Hassanpour, Y, et al.
Argitaratua: (2017)

Synthetic and computational studies on the tricarboxylate core of 6,7-dideoxysqualestatin H5 involving a carbonyl ylide cycloaddition-rearrangement.
nork: Hodgson, D, et al.
Argitaratua: (2010)

An enantioselective epoxide rearrangement - Claisen rearrangement approach to prostaglandins and (+)-iridomyrmecin
nork: Hodgson, D, et al.
Argitaratua: (1997)

Development of asymmetric cycloaddition chemistry.
nork: Hodgson, D, et al.
Argitaratua: (2001)

Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids
nork: Sintim, H, et al.
Argitaratua: (2019)

A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
nork: Kay M. Brummond, et al.
Argitaratua: (2010-04-01)

Cycloaddition of Benzyne with Alkoxy-Substituted Pyrroline-N-oxides: Unexpected Rearrangement to an N-Phenylpyrrole
nork: Franca M. Cordero, et al.
Argitaratua: (2018-01-01)

Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids
nork: Herman O. Sintim, et al.
Argitaratua: (2019-05-01)

Synthesis and Claisen rearrangement of bridged bicyclic enol ethers of relevance to the course of ketene s-cis-diene cycloaddition.
nork: Robertson, J, et al.
Argitaratua: (2006)

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition
nork: Hodgson, D, et al.
Argitaratua: (1997)

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition
nork: Stupple, P, et al.
Argitaratua: (1999)

Chapter 2: Cycloadditions of carbonyl ylides derived from diazocarbonyl compounds
nork: Hodgson, D, et al.
Argitaratua: (2013)

Enantioselective intramolecular 1,3-dipolar cycloadditions of diazocarbonyl-derived oxidopyryliums
nork: Hodgson, D, et al.
Argitaratua: (2003)

An epoxide rearrangement-radical rearrangement approach to 6-substituted 2-azabicyclo[2.2.1]-5-heptenes: Synthesis of an epibatidine analogue
nork: Hodgson, D, et al.
Argitaratua: (1998)

An epoxide rearrangement - Radical rearrangement approach to 6-substituted 2-azabicyclo[2.2.1]-5-heptenes: Synthesis of an epibatidine analogue.
nork: Maxwell, C, et al.
Argitaratua: (1999)

A remarkable base-induced rearrangement of epoxydisilanes
nork: Hodgson, D, et al.
Argitaratua: (1996)

Enantioselective rearrangement of exo-norbornene oxide to nortricyclanol
nork: Hodgson, D, et al.
Argitaratua: (1996)

Enantioselective alpha-deprotonation-rearrangement of meso-epoxides
nork: Hodgson, D, et al.
Argitaratua: (1996)

Enantioselective intramolecular 1,3-dipolar cycloadditions of diazocarbonyl-derived oxidopyryliums
nork: David M. Hodgson, et al.
Argitaratua: (2003-04-01)

Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl
nork: Zhurakovskyi, O, et al.
Argitaratua: (2017)

Tandem intermolecular radical addition-rearrangement for azacycle synthesis
nork: Hodgson, D, et al.
Argitaratua: (2004)

Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides.
nork: Hodgson, D, et al.
Argitaratua: (2003)

The scope of catalytic enantioselective tandem carbonyl ylide formation-intramolecular [3 + 2] cycloadditions.
nork: Hodgson, D, et al.
Argitaratua: (2003)

Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions
nork: Bailey, J, et al.
Argitaratua: (1997)

Oxapolycycles from one-pot cross-metathesis/carbonyl ylide formation-intramolecular cycloaddition of alpha-diazo-beta-keto esters
nork: Hodgson, D, et al.
Argitaratua: (2006)

Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update
nork: Franca Maria Cordero, et al.
Argitaratua: (2024-08-01)

Cycloaddition reaction of heterocumulenes/
nork: 426158 Ulrich, Henri
Argitaratua: (1967)

Enantioselective cycloaddition reactions
nork: Willis, M
Argitaratua: (2008)

Cycloaddition reactions of porphyrins
nork: José A. S. Cavaleiro, et al.
Argitaratua: (2003-10-01)

Synthesis of azabicyclic systems using nitrogen-directed radical rearrangements.
nork: Hodgson, D, et al.
Argitaratua: (2007)

Enantioselective access to isoquinuclidines by tropenone desymmetrization and homoallylic radical rearrangement: synthesis of (+)-ibogamine.
nork: Hodgson, D, et al.
Argitaratua: (2005)