Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization

Koch, Eva; Studer, Armido

doi:10.1002/anie.201300259

Cited by 30 publications

(16 citation statements)

References 57 publications

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“…On treatment of 3 a′ with meta‐ chloroperbenzoic acid, benzofuryl alcohol 15 was prepared, which can be used as a dienophile for [4+3] cycloaddition to afford fused 5,7,6‐tricyclic skeleton present in the various natural products . The synthesis of benzene derivatives bearing several unique substituents are of immense importance and is a challenging synthetic task . Simple hydrolysis of compound 5 a provided α , β ‐unsaturated carboxylic acid 16 , a potent structural analogue for various biologically active molecules .…”

Section: Figurementioning

confidence: 99%

Cobalt(III)‐Catalyzed Construction of Benzofurans, Benzofuranones and One‐Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

et al. 2018

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Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5-exo-dig intramolecular hydroarylation using the amide-directed, cost-effective, high-valent Cp*Co III -catalytic system. Challenging one-pot, orthogonal CÀH functionalizations using two different electrophiles are also reported to afford polysubstituted benzofurans. Several valuable functional group interconversions along with removal of the amide directing group provide a route to access several diversely functionalized benzofurans. The mechanistic study suggests a reversible cobaltation step is operative here.

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Section: Figurementioning

confidence: 99%

Cobalt(III)‐Catalyzed Construction of Benzofurans, Benzofuranones and One‐Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

et al. 2018

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“…Initially, we investigated their regio‐ and stereoselective oxidations with singlet oxygen [9,10] . Later on, we developed a two‐step substitution of aromatic carboxylic acids, [11] which was extended by Studer for palladium‐catalyzed functionalizations [12] . Very recently, we described first Birch reductions in the presence of chloroacetonitrile in a communication (Scheme 1a) [13] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Krüger

Linker

2021

Eur J Org Chem

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A convenient method for the synthesis of γ‐spirolactams in only three steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of chloroacetonitrile affords nitriles in moderate to good yields. Suitable precursors are methyl‐substituted benzoic acids, naphthoic, and anthroic acid. Subsequent catalytic hydrogenation proceeds smoothly with PtO2 or Raney Ni as catalysts and lactams are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation at different pressures, affording products with 0, 1, or 2 double bonds. Overall, more than 15 new γ‐spirolactams have been synthesized in analytically pure form.

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“…Recently, we developed a Pd‐catalyzed stereospecific decarboxylative coupling of substituted 1,4‐cyclohexadiene‐3‐carboxylic acids with aryl iodides leading to 5‐arylated 1,3‐cyclohexadiene derivatives 12a,b. Decarboxylative γ‐arylation was also successfully applied to the total synthesis of resveratrol‐based natural products 12c.…”

Section: Methodsmentioning

confidence: 99%

Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues

Klotter

Studer

2015

Angew Chem Int Ed

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Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key features of the novel strategy are a stereospecific palladium-catalyzed decarboxylative arylation and a one-pot sequence comprising a stereoselective hydroboration followed by oxidation or reduction of the corresponding intermediary boranes. The divergent approach is convincingly demonstrated by the five-step syntheses of (+)-machaeriol B, (+)-machaeriol D, and related analogues, and the four-step synthesis of (+)-Δ(8)-THC and an analogue.

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Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization

Cited by 30 publications

References 57 publications

Cobalt(III)‐Catalyzed Construction of Benzofurans, Benzofuranones and One‐Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Cobalt(III)‐Catalyzed Construction of Benzofurans, Benzofuranones and One‐Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues

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Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization

Cited by 30 publications

References 57 publications

Cobalt(III)‐Catalyzed Construction of Benzofurans, Benzofuranones and One‐Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Cobalt(III)‐Catalyzed Construction of Benzofurans, Benzofuranones and One‐Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ8‐THC, and Analogues

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Product

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Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues