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...

Бүрэн тодорхойлолт

Номзүйн дэлгэрэнгүй
Үндсэн зохиолч:	Fegheh-Hassanpour, Y
Бусад зохиолчид:	Hodgson, D
Формат:	Дипломын ажил
Хэл сонгох:	English
Хэвлэсэн:	2018
Нөхцлүүд:	Organic chemistry

Ижил төстэй зүйлс

Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling
-н: Fegheh-Hassanpour, Y, зэрэг
Хэвлэсэн: (2017)

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

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

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition
-н: Hodgson, D, зэрэг
Хэвлэсэн: (1997)

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition
-н: Stupple, P, зэрэг
Хэвлэсэн: (1999)

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

Chapter 2: Cycloadditions of carbonyl ylides derived from diazocarbonyl compounds
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2013)

Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2000)

Alkene protection against acid using a bromide substituent: application in a total synthesis of (−)-6,7-dideoxysqualestatin H5
-н: Almohseni, H, зэрэг
Хэвлэсэн: (2018)

Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides.
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2003)

The scope of catalytic enantioselective tandem carbonyl ylide formation-intramolecular [3 + 2] cycloadditions.
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2003)

1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides and alkynylbenziodoxoles for synthesis of functional dibenzoullazines
-н: Han, Hui, зэрэг
Хэвлэсэн: (2024)

Development of dirhodium(II)-catalyzed generation and enantioselective 1,3-dipolar cycloaddition of carbonyl ylides.
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2001)

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives
-н: Adam G. Meyer, зэрэг
Хэвлэсэн: (2016-07-01)

Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2004)

1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts
-н: Li, Qiang-Qiang, зэрэг
Хэвлэсэн: (2022)

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds
-н: Radell Echemendía, зэрэг
Хэвлэсэн: (2024-12-01)

Investigation of the Pyridinium Ylide—Alkyne Cycloaddition as a Fluorogenic Coupling Reaction
-н: Simon Bonte, зэрэг
Хэвлэсэн: (2016-03-01)

Catalytic enantioselective intermolecular cycloadditions of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkene dipolarophiles.
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2004)

Catalytic enantioselective tandem carbonyl ylide formation-intramolecular cycloaddition with unsaturated alpha-diazo-beta,epsilon-diketo sulfones
-н: Hodgson, D, зэрэг
Хэвлэсэн: (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
-н: Luis R. Domingo, зэрэг
Хэвлэсэн: (2022-10-01)

[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
-н: Stephan Cludius-Brandt, зэрэг
Хэвлэсэн: (2013-08-01)

[3+2] cycloaddition reactions of arylacetylenes with carbonyl ylides derived from 1-aryl-1-diazohexane-2,5-diones
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2002)

Extended scope of dirhodium(II)-catalysed enantioselective intramolecular 1,3-dipolar cycloadditions of carbonyl ylides with alkene and alkyne dipolarophiles
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2003)

Oxapolycycles from one-pot cross-metathesis/carbonyl ylide formation-intramolecular cycloaddition of alpha-diazo-beta-keto esters
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2006)

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

The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights.
-н: Costel Moldoveanu, зэрэг
Хэвлэсэн: (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
-н: Hodgson, D, зэрэг
Хэвлэсэн: (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
-н: Tayebeh Sattaei Mokhtari, зэрэг
Хэвлэсэн: (2019-12-01)

Catalytic enantioselective intermolecular cycloadditions of a 2-diazo-3,6-diketoester-derived carbonyl ylide with alkyne and strained alkene dipolarophiles
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2003)

Concise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition.
-н: Hodgson, D, зэрэг
Хэвлэсэн: (2002)

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

Intramolecular Heck couplings of unactivated alkyl electrophiles : synthetic and mechanistic studies
-н: Firmansjah, Luke
Хэвлэсэн: (2008)

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

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin
-н: Margareta Sohora, зэрэг
Хэвлэсэн: (2020-06-01)

Expanding the Library of Covalent Cysteine Cathepsin Probes Featuring Sulfoxonium Ylide Electrophiles
-н: Bangyan Xu, зэрэг
Хэвлэсэн: (2024-10-01)

Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis
-н: Sadayuki Arimori, зэрэг
Хэвлэсэн: (2016-01-01)

Efficient Rh-II binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation-cycloaddition of alpha-diazo-beta-keto esters
-н: Hodgson, D, зэрэг
Хэвлэсэн: (1999)

Some investigations of phosphorus ylides
-н: Bradley, Anthony Francis
Хэвлэсэн: (1984)

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