Stereoselective Syntheses of the Octahydropyrano[2,3‐<i>b</i>]pyridine DE Core of 'Upenamide via a Stannous Chloride‐Induced Deacetalisation–Cyclisation Procedure

Ménard‐Moyon, Cécilia; Taylor, Richard J.K.

doi:10.1002/ejoc.200700221

Cited by 14 publications

(6 citation statements)

References 13 publications

(27 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To the best of our knowledge, these studies constitute the first examples of a Fe-catalyzed carbohydroxylation/carbomethoxylation of these olefins. Overall, our results demonstrate that for vinyl pyrrolidinone and vinyl oxazolidinone, the putative N -acyliminium intermediates can be effectively trapped by a nucleophile to yield the corresponding carbohydroxylation/carbomethoxylation products, which are frameworks found in several natural products and useful advanced intermediates. ,− In the case of styrenes, in contrast to a literature report, only a small excess of the starting olefin was required for effective Fe(II)-catalyzed carbohydroxylation or carbomethoxylation.…”

Section: Discussionmentioning

confidence: 51%

Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone

2019

View full text Add to dashboard Cite

The arylative oxygenation of the electron-rich olefins styrene, α-methylstyrene, vinyl pyrrolidinone, and vinyl oxazolidinone was accomplished using arenediazonium salts and catalytic amounts of FeSO4 in an effective single electron transfer radical process. A broad range of aryldiazonium salts was tolerated using water, methanol, or their combination with acetonitrile to furnish the corresponding carbohydroxylated and carbomethoxylated products (42 examples), including functionalized dihydroisocoumarin and dihydrobenzofuran systems in good to excellent yields (up to 88%). The protocols developed for the Fe(II)-catalyzed carbohydroxylation were also compared to Ru(II) and Ir(III) photoredox carbooxygenations of these electron-rich olefins. The Fe(II)-catalyzed process proved to be highly competitive compared to the photoredox and the uncatalyzed processes. The proposed mechanism for the Fe(II)-catalyzed reactions involves the synergic combination with an effective Fe+2/Fe+3 redox system and a radical polar crossover mechanism featuring an unprecedented capture of the reactive N-acyliminium in the case of vinyl pyrrolidinone and vinyl oxazolidinone.

show abstract

Section: Discussionmentioning

confidence: 51%

Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone

2019

View full text Add to dashboard Cite

show abstract

“…Treatment of sulfide 5 with NCS, followed by reaction of the ensuing α-chloro sulfide with the alkynylzinc bromide obtained from alkyne 4 , furnished an inconsequential, epimeric, inseparable mixture of propargyl sulfides 14 (75%, dr = 5.5:4.5). Deprotection of the acetonide afforded diol 15 , which, upon selective monoprotection, yielded pivalate 16 . Oxidation of the sulfide to sulfoxide, followed by [2,3] sigmatropic rearrangement, furnished unsaturated ketone 3 .…”

mentioning

confidence: 99%

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Nyalata

Raghavan

2019

Org. Lett.

View full text Add to dashboard Cite

A convergent stereoselective route to the C16–C37 fragment of sorangicin A is disclosed using an α-chloro sulfide for C–C bond formation. The key intermediate, an α,β-unsaturated ketone, is revealed by a [2,3] sigmatropic rearrangement of a propargylic sulfoxide. Three disparate approaches are detailed to create the C25 carbinol stereocenter. The cis-2,6-disubstitution of the THP ring is secured by ionic hydrogenation. A cross-metathesis reaction and Julia–Kocienski olefination furnish the C16–C37 fragment of sorangicin A.

show abstract

“…Moreover, new applications in the synthesis of non-β-lactam molecules of biological significance have also been discovered. , Although the tetrahydrofuran structural unit is abundant in bioactive natural and synthetic molecules, very few examples of C-fused tetrahydrofuro-β-lactams are known in the literature. They are mostly tetrahydrofuro[2,3- c ]azetidin-2-ones having a C3−O linkage. − , The isomeric tetrahydrofuro[3,2- c ]azetidin-2-ones with a C4−O linkage which are also isomeric to oxapenams are scarcely known …”

mentioning

confidence: 99%

Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c]azetidin-2-ones

2010

View full text Add to dashboard Cite

Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused β-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.

show abstract

Stereoselective Syntheses of the Octahydropyrano[2,3‐b]pyridine DE Core of 'Upenamide via a Stannous Chloride‐Induced Deacetalisation–Cyclisation Procedure

Cited by 14 publications

References 13 publications

Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone

Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone

Convergent Stereoselective Synthesis of the C16–C37 Subunit of Sorangicin A

Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c]azetidin-2-ones

Contact Info

Product

Resources

About