Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling

Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling

An asymmetric synthesis of (−)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include: (1) highly diastereoselective n-alkylation of a tartrate acetonide enolate and subsequent oxidation−hydrolysis to provide an asymmetric entry to a β-hydroxy-α-ketoester motif; (2) facilitati...

Πλήρης περιγραφή

Λεπτομέρειες βιβλιογραφικής εγγραφής
Κύριοι συγγραφείς:	Fegheh-Hassanpour, Y, Arif, T, Sintim, H, Al Mamari, H, Hodgson, D
Μορφή:	Journal article
Έκδοση:	American Chemical Society 2017

Παρόμοια τεκμήρια

Total synthesis of (–)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition and cross–electrophile coupling
ανά: Fegheh-Hassanpour, Y
Έκδοση: (2018)

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

Alkene protection against acid using a bromide substituent: application in a total synthesis of (−)-6,7-dideoxysqualestatin H5
ανά: Almohseni, H, κ.ά.
Έκδοση: (2018)

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition
ανά: Hodgson, D, κ.ά.
Έκδοση: (1997)

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition
ανά: Stupple, P, κ.ά.
Έκδοση: (1999)

Chapter 2: Cycloadditions of carbonyl ylides derived from diazocarbonyl compounds
ανά: Hodgson, D, κ.ά.
Έκδοση: (2013)

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

Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins
ανά: Hodgson, D, κ.ά.
Έκδοση: (2000)

Catalytic enantioselective rearrangements and cycloadditions involving ylides from diazo compounds
ανά: Hodgson, D, κ.ά.
Έκδοση: (2000)

Catalytic enantioselective rearrangements and cycloadditions involving ylides from diazo compounds
ανά: Hodgson, D, κ.ά.
Έκδοση: (2001)

Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2003)

The scope of catalytic enantioselective tandem carbonyl ylide formation-intramolecular [3 + 2] cycloadditions.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2003)

Development of dirhodium(II)-catalyzed generation and enantioselective 1,3-dipolar cycloaddition of carbonyl ylides.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2001)

Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2004)

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives
ανά: Adam G. Meyer, κ.ά.
Έκδοση: (2016-07-01)

Catalytic enantioselective tandem carbonyl ylide formation-intramolecular cycloaddition with unsaturated alpha-diazo-beta,epsilon-diketo sulfones
ανά: Hodgson, D, κ.ά.
Έκδοση: (2009)

Catalytic enantioselective intermolecular cycloadditions of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkene dipolarophiles.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2004)

Oxapolycycles from one-pot cross-metathesis/carbonyl ylide formation-intramolecular cycloaddition of alpha-diazo-beta-keto esters
ανά: Hodgson, D, κ.ά.
Έκδοση: (2006)

[3+2] cycloaddition reactions of arylacetylenes with carbonyl ylides derived from 1-aryl-1-diazohexane-2,5-diones
ανά: Hodgson, D, κ.ά.
Έκδοση: (2002)

Extended scope of dirhodium(II)-catalysed enantioselective intramolecular 1,3-dipolar cycloadditions of carbonyl ylides with alkene and alkyne dipolarophiles
ανά: Hodgson, D, κ.ά.
Έκδοση: (2003)

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

Concise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2002)

Catalytic enantioselective intermolecular cycloadditions of a 2-diazo-3,6-diketoester-derived carbonyl ylide with alkyne and strained alkene dipolarophiles
ανά: Hodgson, D, κ.ά.
Έκδοση: (2003)

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
ανά: Sintim, H, κ.ά.
Έκδοση: (2019)

Synthesis and evaluation of 4,4 ',6,6 '-tetrasubstituted binaphtholphosphate dirhodium(II) complexes as catalysts in enantioselective carbonyl ylide formation-cycloaddition reactions
ανά: Hodgson, D, κ.ά.
Έκδοση: (2003)

Efficient Rh-II binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation-cycloaddition of alpha-diazo-beta-keto esters
ανά: Hodgson, D, κ.ά.
Έκδοση: (1999)

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

Investigation of the Pyridinium Ylide—Alkyne Cycloaddition as a Fluorogenic Coupling Reaction
ανά: Simon Bonte, κ.ά.
Έκδοση: (2016-03-01)

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
ανά: Luis R. Domingo, κ.ά.
Έκδοση: (2022-10-01)

A cycloaddition-rearrangement approach to the squalestatins
ανά: Hodgson, D, κ.ά.
Έκδοση: (1996)

The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights.
ανά: Costel Moldoveanu, κ.ά.
Έκδοση: (2016-01-01)

1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles
ανά: John H. Ryan
Έκδοση: (2015-01-01)

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin
ανά: Margareta Sohora, κ.ά.
Έκδοση: (2020-06-01)

Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.
ανά: Hodgson, D, κ.ά.
Έκδοση: (2011)

Expanding the Library of Covalent Cysteine Cathepsin Probes Featuring Sulfoxonium Ylide Electrophiles
ανά: Bangyan Xu, κ.ά.
Έκδοση: (2024-10-01)

Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis
ανά: Sadayuki Arimori, κ.ά.
Έκδοση: (2016-01-01)

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
ανά: Tayebeh Sattaei Mokhtari, κ.ά.
Έκδοση: (2019-12-01)

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
ανά: Herman O. Sintim, κ.ά.
Έκδοση: (2019-05-01)

On the ozonolysis of unsaturated tosylhydrazones as a direct approach to diazocarbonyl compounds
ανά: Fegheh-Hassanpour, Y, κ.ά.
Έκδοση: (2018)

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