Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives

Nakajima, Masaya; Kondo, Yûsuke; Nakano, Shun‐ichi; Adachi, Yusuke; Choi, Dongil; Franzén, Robert; Nemoto, Tetsuhiro

doi:10.1016/j.tetlet.2020.151754

Cited by 2 publications

(2 citation statements)

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“…Acetylation of 80 a.3 produced 80 a.4 followed by the removal of the acetoxy group through NaBH 4 , afforded 80 a.5 (Scheme 53). [182] Radical cascade cyclization in the presence of HSnBu 3 produced 80 a.6 . Finally, the important bioactive core 80 a analogous to radermachol was obtained in 92 % yield by the treatment of excess trifluoacetic acid.…”

Section: Synthetic Routes Toward Fused Furanmentioning

confidence: 99%

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A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

Manna¹,

Giri

Mondal³

et al. 2023

ChemistrySelect

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c‐fused furan and their derivatives are widely used as essential components of agrochemicals, bioregulators, dyes, essential skin and hair oils, cosmetics, flavouring agents, photosensitizers in industry and also show a broad range of biological activity. To the best of our knowledge, as of yet, no review has been published that covers the entire synthetic pathway leading to the formation of just c‐fused or 3, 4‐fused furans. In this review, we outline the various pathways for bicyclic, tricyclic, and polycyclic c‐fused furans, along with their detailed mechanisms, concrete examples, and biological activity. We have focused particularly on the synthetic route to medicine, natural products, and their analogues, such as c‐fused furanoditerpenes isospongiadiol, radermachol, a potential folk medicine ingredient, furo[3,4]quinolin‐4(5H)‐ones core, an inhibitor of lymphoma, bhimamycin B, hibiscone‐c core moiety of antibiotic lactonamycin, and analogue of natural product furanether A/ furanether B. Previous approaches and recent methods are described including metal‐free, transition metal, bio‐catalyst, and multi‐substrate approaches with mechanisms. The review covers the literature for more than six decades and presents an overview of the synthesis of different c‐fused furans and their utility in various disciplines such as synthetic chemistry, medicinal chemistry, and drug discovery.

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Section: Synthetic Routes Toward Fused Furanmentioning

confidence: 99%

“…). [182] Radical cascade cyclization in the presence of HSnBu 3 produced 80 a.6. Finally, the important bioactive core 80 a analogous to radermachol was obtained in 92 % yield by the treatment of excess trifluoacetic acid.…”

Section: In Catalystmentioning

confidence: 99%