Concise Total Synthesis of rac-Betuphenone F

Nguyen Ngoc Thanh Luan; Takuya Okada; Naoki Toyooka

doi:10.1002/ejoc.202300047

Concise Total Synthesis of rac-Betuphenone F

Nguyen Ngoc Thanh Luan, Takuya Okada^*, Naoki Toyooka

^*Corresponding author for this work

Life Sciences and Bioengineering

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

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.

Original language	English
Article number	e202300047
Journal	European Journal of Organic Chemistry
Volume	26
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.202300047
State	Published - 2023/03/21

Keywords

2-oxabicyclo[3.3.1]nonane
anti-austerity
anti-cancer
betuphenone
total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/ejoc.202300047

Cite this

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title = "Concise Total Synthesis of rac-Betuphenone F",

abstract = "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.",

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author = "Luan, {Nguyen Ngoc Thanh} and Takuya Okada and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = mar,

day = "21",

doi = "10.1002/ejoc.202300047",

language = "英語",

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journal = "European Journal of Organic Chemistry",

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AU - Luan, Nguyen Ngoc Thanh

AU - Okada, Takuya

AU - Toyooka, Naoki

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Y1 - 2023/3/21

N2 - 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.

AB - 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.

KW - 2-oxabicyclo[3.3.1]nonane

KW - anti-austerity

KW - anti-cancer

KW - betuphenone

KW - total synthesis

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Concise Total Synthesis of rac-Betuphenone F

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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