Synthesis of Carborane-Fused Lactones via Electrochemical C( <i>sp</i> <sup>3</sup> )–H Lactonization: Access to Benzofused Lactone Bioisosteres

The replacement of the benzene ring with its bioisosteres is a powerful strategy in drug discovery, yet the development of <i>ortho</i>-disubstituted benzene bioisosteres, particularly fused-ring systems, remains underexplored. Herein, we report an electrooxidative protocol for the synthesis of carborane-fused lactones via C(<i>sp</i><sup>3</sup>)-H lactonization. This protocol provides concise access to carborane-fused γ- and δ-lactone frameworks, which closely mimic the geometric features of benzofused lactones, thereby underscoring their potential as bioisosteres of benzofused lactones.

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Publication Details

Journal
Organic Letters
Published
2025-12-24
DOI
https://doi.org/10.1021/acs.orglett.5c04750
Primary Topic
Boron Compounds in Chemistry
Type
article
Field-Weighted Citation Impact
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article

Synthesis of Carborane-Fused Lactones via Electrochemical C( sp 3 )–H Lactonization: Access to Benzofused Lactone Bioisosteres

Phil Ho Lee, HyeonMi Cho, Kyungsup Lee, Hee Chan Noh et al.
Organic Letters
Boron Compounds in Chemistry
article

Synthesis of Carborane-Fused Lactones via Electrochemical C( sp 3 )–H Lactonization: Access to Benzofused Lactone Bioisosteres

Phil Ho Lee, HyeonMi Cho, Kyungsup Lee, Hee Chan Noh, Yohan Park, Jee Eun Hong, Euijae Lee, Yurim Park
article en

Abstract

The replacement of the benzene ring with its bioisosteres is a powerful strategy in drug discovery, yet the development of <i>ortho</i>-disubstituted benzene bioisosteres, particularly fused-ring systems, remains underexplored. Herein, we report an electrooxidative protocol for the synthesis of carborane-fused lactones via C(<i>sp</i><sup>3</sup>)-H lactonization. This protocol provides concise access to carborane-fused γ- and δ-lactone frameworks, which closely mimic the geometric features of benzofused lactones, thereby underscoring their potential as bioisosteres of benzofused lactones.

Organic LettersVol. 28(1)
Kangwon National University (KR), Chungnam National University (KR), International Drug Development (FR)
Openalex Percentile: Top 31%
Boron Compounds in Chemistry
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Synthesis of Carborane-Fused Lactones via Electrochemical C( <i>sp</i> <sup>3</sup> )–H Lactonization: Access to Benzofused Lactone Bioisosteres — Phil Ho Lee, HyeonMi Cho, et al. · Organic Letters (2025) | TGRS Research Map | TGRS