Concise Total Synthesis of rac‐Betuphenone F

Betuphenone F (6) is a natural product isolated from the bark of Betula alnoides Ham. ex D. Don (Betulaceae) and structurally determined by S. Awale et al. in 2021. Betuphenone F (6) has the potential to be a new‐generation anti‐cancer agents based on anti‐austerity, as it showed preferential cytoto...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-03, Vol.26 (12), p.n/a
Main Authors: Luan, Nguyen Ngoc Thanh, Okada, Takuya, Toyooka, Naoki
Format: Article
Language:English
Subjects:
2-oxabicyclo[3.3.1]nonane
anti-austerity
anti-cancer
betuphenone
Cancer
Natural products
Phloroglucinol
Synthesis
total synthesis
Toxicity
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Summary:Betuphenone F (6) is a natural product isolated from the bark of Betula alnoides Ham. ex D. Don (Betulaceae) and structurally determined by S. Awale et al. in 2021. Betuphenone F (6) has the potential to be a new‐generation anti‐cancer agents based on anti‐austerity, as it showed preferential cytotoxicity against PANC‐1 human pancreatic cancer cells under nutrient‐deprived conditions (PC50 value of 4.9 μM). We succeeded in constructing the 2‐oxabicyclo[3.3.1]nonane skeleton, which is a structural feature of betuphenone F (6), by exposing intermediate 9 to acid, and achieved the first total synthesis of rac‐bethuphenone F (6) from phloroglucinol (7) in only three steps. Betuphenone F, a natural product isolated from the bark of Betula alnoides Ham. ex D. Don, has the potential to be a new‐generation anti‐cancer agents based on anti‐austerity. We succeeded in constructing the 2‐oxabicyclo[3.3.1]nonane skeleton, a structural feature of betuphenone F, and achieved the first total synthesis of rac‐bethuphenone F from phloroglucinol in three steps.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300047