Synthesis of sulfur-containing polybromoindoles from the marine alga Laurencia brongniartii

Article Chemistry, Organic

Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions

Peng Qi et al.

Summary: This study describes a base-free bis-alkyl thiolation reaction using sulfinothioates as thiolation reagents, enabling double C-H thiolation at the C2 and C3 of indoles in one pot.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of Axially Chiral 3,3'-Bisindoles by Direct Coupling of Indole Rings

Feng-Tao Sheng et al.

Summary: A new strategy for the enantioselective synthesis of axially chiral 3,3'-bisindoles was developed by directly coupling two indole rings using the C3-umpolung reactivity of 2-indolylmethanols. The synthesized compounds can be further modified to create axially chiral 3,3'-bisindole-based organocatalysts for asymmetric catalysis.

CHINESE JOURNAL OF CHEMISTRY (2022)

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Article Chemistry, Organic

Synthetic Studies toward Bisindigotin: Polyheteroaromatic Scaffolds via Skeletal Rearrangements of a Diacetoxytetraindole

Maurycy Prystupa et al.

Summary: The deacetylation of a diacetoxytetraindole led to unexpected results in the synthetic route towards the alkaloid bisindigotin, forming novel nine-ring heteroaromatic scaffolds. Acid-mediated hydrolysis triggered skeletal rearrangement, while treatment with base and silica-mediated autoxidation generated another novel nine-ring scaffold through a distinct cascade process. Mechanistic rationale for these observations was provided.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization

Leiyang Bai et al.

Summary: Through a one-step catalytic operation, this study successfully designed a synthetic pathway for the total synthesis of isocalycanthine and its derivatives, which possess novel structures and alkaloid activities in dimeric cyclotryptamine alkaloids.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Methylthiolation for Electron-Rich Heteroarenes with DMSO-TsCl

Lei-Yang Zhang et al.

Summary: DMSO-TsCl has been developed as a novel reagent for direct methylthiolation of various electron-rich heteroarenes with high regioselectivity in moderate to excellent yields, especially for pyrroles, furans, and thiophenes. This practical method is scalable, metal-free, and operates under mild conditions, demonstrating compatibility with air and moisture. The methylthiolated products of this reaction have shown diverse applications, with a proposed mechanism supported by controlled experimental results and key intermediates detected by HRMS.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

Yuanbo Du et al.

Summary: This study demonstrates a facile method for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide, with mild reaction conditions and a broad range of substrates. Efficient bromination of ortho C-H bonds of the aryhydroxylamines was achieved, resulting in good to excellent yields of ortho-bromoanilide products. Model scaled-up reactions of this synthetic approach were also shown in this work.

TETRAHEDRON LETTERS (2021)

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Article Chemistry, Organic