Unlocking Diversity: From Simple to Cutting-Edge Synthetic Methodologies of Bis(indolyl)methanes

Teli, Pankaj; Soni, Shivani; Teli, Sunita; Agarwal, Shikha

doi:10.1007/s41061-024-00454-z

Cited by 7 publications

(2 citation statements)

References 199 publications

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“…The diverse array of natural 2,3′-bis(indolyl)methane (2,3′-BIM) alkaloids offers access to new and exciting chemical scaffolds, demonstrating the potential for the development of drugs possessing significant anticancer and anticholinesterase activities. 1 , 2 Among the various 2,3′-BIM skeletons, derivatives of 3-(indol-2-yl)-3-(indol-3-yl)-1,2-propanediol (IIPDO) containing two chiral carbons emerge as particularly appealing entities ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative

Saetae,

Chantana,

Saithong

et al. 2024

J. Org. Chem.

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The short and first total synthesis of (+)-colletotryptins B-D, ent-colletotryptin A, and diastereomer of mucronatin B, which are a group of natural 3-(indol-2-yl)-3-(indol-3-yl)-1,2-propanediol (IIPDO) analogues containing two stereogenic centers at the C8′ and C9′ positions, isolated from endophytic fungus Colletotrichum sp. SC1355 and Tetrapterys mucronata, respectively, has been successfully accomplished in two and three steps with overall yields ranging from 28 to 54%. Key features of this synthesis include an innovative Bi(OTf) 3 -catalyzed stereoselective transindolylation of (S)-3,3′-di(1H-indol-3-yl)propane-1,2-diol. The operational simplicity, environmentally friendly catalyst, and broad functional group tolerance of this modular strategy render it suitable for adoption in both academic and industrial settings.

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Section: Introductionmentioning

confidence: 99%

Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative

Saetae,

Chantana,

Saithong

et al. 2024

J. Org. Chem.

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“…In addition, O -heterocycle 10 was obtained in 92% yield on conversion of the benzaldehyde motif in 2a to the benzonitrile group with Ph 2 P(O)ONH 2 in toluene at 80 °C for 4 h (Scheme g) . In a final experiment, InBr 3 -catalyzed Friedel–Crafts arylation of 2a with 1 H -indole in 1,2-dichloroethane at room temperature for 12 h was demonstrated to afford the bis(indolyl)methane-substituted furan 11 in 90% yield (Scheme h) …”

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confidence: 99%

Rhodium(I)-Catalyzed Cascade Annulation of 1,n-Diynyl Nitrones to 3,4-Fused Fully Substituted Furans

Yu,

Ji,

Shang

et al. 2024

Org. Lett.

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Diaryliodonium Salt‐Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes

Wang,

Jiang,

Lin

et al. 2024

Adv Synth Catal

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A method for the synthesis of unsymmetrical bis(indolyl)methanes (BIMs) using simple indoles and readily available alcohols as the coupling partners under both heat and 390–400 nm light conditions was developed. Detailed research of the mechanism demonstrated that the diaryliodonium salt‐mediated transformation undergoes a nucleophilic hydroxymethyl radical formation process. Moreover, the diaryliodonium salt‐mediated method is also applicable for synthesizing symmetrical BIMs.

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Unlocking Diversity: From Simple to Cutting-Edge Synthetic Methodologies of Bis(indolyl)methanes

Cited by 7 publications

References 199 publications

Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative

Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative

Rhodium(I)-Catalyzed Cascade Annulation of 1,n-Diynyl Nitrones to 3,4-Fused Fully Substituted Furans

Diaryliodonium Salt‐Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes

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