Total Synthesis of Lineaflavones A, C, D, and Analogues.

Rui Wang, Yu Fu, Ran Ma, Hongzhen Jin, Wei Zhao

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Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Rui WangState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, China.

Yu FuState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, China.

Ran MaState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, China.

Hongzhen JinState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, China.

Wei ZhaoState Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Key Laboratory of Molecular Drug Research and KLMDASR of Tianjin, Nankai University, Tongyan Road, Haihe Education Park, Tianjin 300350, China.

Funding

National Key R&D Program of China 2018YFA0507204National Natural Science Foundation of China 22077068

6 · The paper itself

Abstract

The first total synthesis of lineaflavones A, C, D, and their analogues has been accomplished. The key synthetic steps include aldol/oxa-Michael/dehydration sequence reactions to assemble the tricyclic core, Claisen rearrangement and Schenck ene reaction to construct the key intermediate, and selective substitution or elimination of tertiary allylic alcohol to obtain natural compounds. In addition, we also explored five new routes to synthesize fifty-three natural product analogues, which can contribute to a systematic structure-activity relationship during biological evaluation.

Indexed as

Biological ProductsStereoisomerismStructure-Activity RelationshipBiological Productsflavonoidsnatural productsschenck ene reactiontotal synthesis

Identifiers

PMID36903616

DOI10.3390/molecules28052373

PMCPMC10005778

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