The first total synthesis of (±)-ribasine

Ollero, Lourdes; Castedo, Luís; Domı́nguez, Domingo

doi:10.1016/s0040-4039(97)10778-x

Cited by 12 publications

(3 citation statements)

References 9 publications

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“…To date, only the Dominguez group 9 has described a successful synthesis of ribasine by a stereocontrolled addition of the 3,4-methylenedioxy-substituted α-lithium- o -toluate ( 5 ) to 2-(9-phenylfluoren-9-yl)-amino-1-indanone ( 6 ). The resulting lactone 7 was reduced and cyclized to ultimately give ribasine 1 (Scheme ) 1 …”

Section: Introductionmentioning

confidence: 99%

Model Studies Directed toward the Total Synthesis of (±)-Ribasine. A Tandem Cyclization−Cycloaddition Route Leading to the Core Skeleton

1999

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A series of R-diazo-β-(o-carbomethoxy)-substituted aryl ketones were prepared and employed as model systems for a synthetic approach toward the alkaloid ribasine. Six-membered ring carbonyl ylide dipoles were generated by treating the diazoketones with a rhodium(II) catalyst. The initially formed dipole was trapped using a variety of dipolarophiles including N-benzylidene methylamine. The Rh(II)-catalyzed behavior of ethyl 2-diazo-3-(2-formylphenyl)-3-oxo-propionate was also studied to probe the chemoselectivity of the reaction. The major products isolated are derived from bimolecular trapping of the carbonyl ylide dipole, as well as intramolecular C-H insertion of the rhodium carbenoid into the aldehydic hydrogen. Changing the catalyst from Rh(II) trifluoroacetate to Rh(II) acetate caused a significant alteration in product distribution. A study of the tandem cyclization-cycloaddition reaction of an o-allyl phenyl substituted diazoketone was also carried out. An unexpected low-temperature intramolecular dipolar cycloaddition of the diazo group across the neighboring π-bond first occurred, followed by nitrogen extrusion to give products derived from a 1,3-biradical intermediate. By subjecting the diazoketone to the Rh(II) catalyst at 110 °C, it was possible to prepare the carbonyl ylide derived cycloadduct in high yield. This result provides good precedent for the future implementation of the cycloaddition strategy toward the synthesis of ribasine.

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Section: Introductionmentioning

confidence: 99%

Model Studies Directed toward the Total Synthesis of (±)-Ribasine. A Tandem Cyclization−Cycloaddition Route Leading to the Core Skeleton

1999

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“…Designated E-2128-1 163, shows an inhibitory effect on 1L-1 production. 87 Andrimide (164), isolated from the natural bacterium Pseudomonas fluorescens has been found to be bacteriostatic towards Gram-(+) and Gram-(2) bacteria and preferentially inhibited RNA polymerase and UMP kinase activities. 88 Microginin 299A and microginin 299B are metabolites produced by the cyanobacterium Microcystis aeruginosa which is a causative agent for bloom in fresh water lakes.…”

Section: Peptide Alkaloidsmentioning

confidence: 99%

“…This synthetic procedure has also been applied to the synthesis of (±)-ribasin 340. 164 Makaluvic acid A 341 and makaluvic acid B 342 are novel alkaloids found in the sponge Zyzzya fuliginosus. 165 Hanishin 343 is a semi-racemic bioactive C 9 alkaloid found in the axinellid sponge Acanthella carterie.…”

Section: Miscellaneous Alkaloidsmentioning

confidence: 99%

Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids

Lewis

2000

Nat. Prod. Rep.

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Synthesis of Five‐ and Six‐Membered Benzocyclic Ketones through Intramolecular Alkene Hydroacylation Catalyzed by Nickel(0)/N‐Heterocyclic Carbenes

et al. 2012

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The first total synthesis of (±)-ribasine

Cited by 12 publications

References 9 publications

Model Studies Directed toward the Total Synthesis of (±)-Ribasine. A Tandem Cyclization−Cycloaddition Route Leading to the Core Skeleton

Model Studies Directed toward the Total Synthesis of (±)-Ribasine. A Tandem Cyclization−Cycloaddition Route Leading to the Core Skeleton

Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids

Synthesis of Five‐ and Six‐Membered Benzocyclic Ketones through Intramolecular Alkene Hydroacylation Catalyzed by Nickel(0)/N‐Heterocyclic Carbenes

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