Total synthesis of (–)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition and cross–electrophile coupling

Total synthesis of (–)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition and cross–electrophile coupling

<p>The work presented in this thesis focuses on the total synthesis of (–)-6,7- Dideoxysqualestatin H5. Particular emphasis was the development of a cross– coupling strategy for direct delivery of the side chain towards the end of the synthesis.</p> <p>Various methods investigated...

Disgrifiad llawn

Manylion Llyfryddiaeth
Prif Awdur:	Fegheh-Hassanpour, Y
Awduron Eraill:	Hodgson, D
Fformat:	Traethawd Ymchwil
Iaith:	English
Cyhoeddwyd:	2018
Pynciau:	Organic chemistry

Eitemau Tebyg

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

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

Carbonyl ylide cycloadditions of dicobalt carbonyl complexes of propargylic aldehydes
gan: Skaggs, Aaron J. (Aaron Jeremy), 1976-
Cyhoeddwyd: (2005)

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

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

Studies towards squalene synthase inhibitors: total synthesis of 6,7-dideoxysqualestatin h5 via an alkene-protection strategy
gan: Almohseni, H
Cyhoeddwyd: (2019)

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

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

Alkene protection against acid using a bromide substituent: application in a total synthesis of (−)-6,7-dideoxysqualestatin H5
gan: Almohseni, H, et al.
Cyhoeddwyd: (2018)

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

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

1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides and alkynylbenziodoxoles for synthesis of functional dibenzoullazines
gan: Han, Hui, et al.
Cyhoeddwyd: (2024)

Development of dirhodium(II)-catalyzed generation and enantioselective 1,3-dipolar cycloaddition of carbonyl ylides.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2001)

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives
gan: Adam G. Meyer, et al.
Cyhoeddwyd: (2016-07-01)

Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts
gan: Li, Qiang-Qiang, et al.
Cyhoeddwyd: (2022)

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds
gan: Radell Echemendía, et al.
Cyhoeddwyd: (2024-12-01)

Investigation of the Pyridinium Ylide—Alkyne Cycloaddition as a Fluorogenic Coupling Reaction
gan: Simon Bonte, et al.
Cyhoeddwyd: (2016-03-01)

Catalytic enantioselective intermolecular cycloadditions of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkene dipolarophiles.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

Catalytic enantioselective tandem carbonyl ylide formation-intramolecular cycloaddition with unsaturated alpha-diazo-beta,epsilon-diketo sulfones
gan: Hodgson, D, et al.
Cyhoeddwyd: (2009)

A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of an Azomethine Ylide with an Electrophilic Ethylene Linked to Triazole and Ferrocene Units
gan: Luis R. Domingo, et al.
Cyhoeddwyd: (2022-10-01)

[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
gan: Stephan Cludius-Brandt, et al.
Cyhoeddwyd: (2013-08-01)

[3+2] cycloaddition reactions of arylacetylenes with carbonyl ylides derived from 1-aryl-1-diazohexane-2,5-diones
gan: Hodgson, D, et al.
Cyhoeddwyd: (2002)

Extended scope of dirhodium(II)-catalysed enantioselective intramolecular 1,3-dipolar cycloadditions of carbonyl ylides with alkene and alkyne dipolarophiles
gan: Hodgson, D, et al.
Cyhoeddwyd: (2003)

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

One-pot cross-metathesis/tandem carbonyl ylide formation-intramolecular cycloaddition of an unsaturated 2-diazo-3,6-diketoester.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2006)

The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights.
gan: Costel Moldoveanu, et al.
Cyhoeddwyd: (2016-01-01)

Synthesis and evaluation of 4,4 ',6,6 '-tetrasubstituted binaphtholphosphate dirhodium(II) complexes as catalysts in enantioselective carbonyl ylide formation-cycloaddition reactions
gan: Hodgson, D, et al.
Cyhoeddwyd: (2003)

Polar [3 + 2] cycloaddition of isatin-3-imines with electrophilically activated heteroaromatic N-ylides: Synthesis of spirocyclic imidazo[1,2-a]pyridine and isoquinoline derivatives
gan: Tayebeh Sattaei Mokhtari, et al.
Cyhoeddwyd: (2019-12-01)

Catalytic enantioselective intermolecular cycloadditions of a 2-diazo-3,6-diketoester-derived carbonyl ylide with alkyne and strained alkene dipolarophiles
gan: Hodgson, D, et al.
Cyhoeddwyd: (2003)

Concise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2002)

The Synthesis of the Hydrogenated Thiophenes by [3+2] Cycloaddition Reaction of Thiocarbonyl Ylide
gan: Tymofii V. Rudenko, et al.
Cyhoeddwyd: (2023-06-01)

Intramolecular Heck couplings of unactivated alkyl electrophiles : synthetic and mechanistic studies
gan: Firmansjah, Luke
Cyhoeddwyd: (2008)

The total synthesis of salvilenon : intramolecular [4+2] cycloadditions of conjugated enzynes
gan: Helgason, Anna Loa
Cyhoeddwyd: (2005)

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin
gan: Margareta Sohora, et al.
Cyhoeddwyd: (2020-06-01)

Expanding the Library of Covalent Cysteine Cathepsin Probes Featuring Sulfoxonium Ylide Electrophiles
gan: Bangyan Xu, et al.
Cyhoeddwyd: (2024-10-01)

Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis
gan: Sadayuki Arimori, et al.
Cyhoeddwyd: (2016-01-01)

Efficient Rh-II binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation-cycloaddition of alpha-diazo-beta-keto esters
gan: Hodgson, D, et al.
Cyhoeddwyd: (1999)

Some investigations of phosphorus ylides
gan: Bradley, Anthony Francis
Cyhoeddwyd: (1984)

Enantioselective [4 + 2] cycloadditions of iminoacetonitriles : application to the total synthesis of (-)-quinolizidine 2071
gan: Fontaine, Shaun D. (Shaun David)
Cyhoeddwyd: (2012)