Total Syntheses of the Elusive Welwitindolinones with Bicyclo[4.3.1] Cores

Huters, Alexander D.; Styduhar, Evan D.; Garg, Neil K.

doi:10.1002/anie.201107567

Cited by 80 publications

(34 citation statements)

References 73 publications

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“…Likewise, the Garg lab reported a synthesis of various Nmethylwelwitindolinones such as 38 82 by means of an indolyne cyclization (Scheme 10). 83,84,85,86,87 Here, indolyne formation is triggered by base-induced halide elimination. The authors note minor issues of competing O-addition of the enolate in intermediate 39.…”

Section: Scheme 8 Retrosynthetic Analysis Of 35 Leads To An Aryne Inmentioning

confidence: 99%

Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

Wright¹

2019

Org. Synth.

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Section: Scheme 8 Retrosynthetic Analysis Of 35 Leads To An Aryne Inmentioning

confidence: 99%

Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

Wright¹

2019

Org. Synth.

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“…[1] In particular,five-and six-membered spirocyclic oxindoles are considered privileged molecular structures associated with variousc ompounds with potent pharmaceutical properties ( Figure 1). [2] The considerable medicinal potential of the spirocyclic oxindole structural motif hasl ed the scientific community to design innovative ande fficient synthetic approaches, [3,4] exploitinge ither metal catalysts or organocatalysts.…”

Section: Introductionmentioning

confidence: 99%

Highly Stereoselective [4+2] and [3+2] Spiroannulations of 2‐(2‐Oxoindolin‐3‐ylidene)acetic Esters Catalyzed by Bifunctional Thioureas

Monari

Montroni

Nitti

et al. 2015

Chemistry A European J

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A new Michael-Michael cascade reaction between 2-(2-oxoindolin-3-ylidene)acetic esters 1 and nitroenoates 2, catalyzed by bifunctional thioureas, is investigated. The combination of the two Michael reactions results in a novel and facile [4+2] or [3+2] spiroannulation process, which is characterized by the following features: 1) two carbon-carbon bonds and four stereocenters, including a quaternary spiro carbon, are formed under mild conditions; 2) an unprecedented and stereochemically defined substitution pattern on the spirocarbocyclic unit is obtained; 3) the double-bond configuration of the donor-acceptor nitroenoate 2 determines the absolute configuration of the spiro center, whereas the remaining stereocenters are formed under control of the catalyst. The effect on the final stereochemical outcome of structural variations of each starting material, catalyst, and experimental conditions is analyzed in detail. In particular, the use of specifically designed chiral nitroenoates enables diverse polyfunctional spirocyclohexane derivatives containing six consecutive stereogenic centers to be constructed. To our knowledge, this is the first asymmetric organocatalytic strategy enabling both five- and six-membered β-nitro spirocarbocyclic oxindoles.

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“…Oxindole frameworks are found in many bioactive compounds and natural products. Due to this synthetic methods and transformations of oxindole skeletons have been extensively investigated [2][3][4][5] . The naturally occurring oxindole derivative convolutamydine has been found to exhibit potent activity in the differentiation of HL-60 human plomyelocyticleukemic cells.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Studies of Colvent Effect for Oxindole Derivatives Using Polarizable Continuum Model

Vidhya¹,

Sathyanarayanamoorthi²,

Kannapan³

2017

Orient. J. Chem

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Oxindole derivatives which are commercially available have got antiviral, antifungal, antibacterial, anticancer, anti-inflammatory, antihypertensive, and anticonvulsant activities. The solvation analysis of oxindole derivatives has been carried out using B3LYP procedure with 6-311++G basis set using ten solvents to compute the electrostatic interaction, repulsive, dispersive energy and cavitation energy respectively. Studies of the electrostatic interaction of four solutes were satisfactorily correlated with dielectric constants of polar solvents. Free energy values for all the four solutes in both polar and non polar solvents were found to be negative. The negative value suggests that dissolution process in thermodynamically are feasible for all the four solutes in the investigated solvent.

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Total Syntheses of the Elusive Welwitindolinones with Bicyclo[4.3.1] Cores

Cited by 80 publications

References 73 publications

Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

Highly Stereoselective [4+2] and [3+2] Spiroannulations of 2‐(2‐Oxoindolin‐3‐ylidene)acetic Esters Catalyzed by Bifunctional Thioureas

Theoretical Studies of Colvent Effect for Oxindole Derivatives Using Polarizable Continuum Model

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