Concise Total Synthesis of rac‐Betuphenone F

Author:

Luan Nguyen Ngoc Thanh1,Okada Takuya2ORCID,Toyooka Naoki2

Affiliation:

1. Faculty of Education and Research Promotion University of Toyama 3190 Gofuku Toyama 930-8555 Japan

2. Faculty of Engineering University of Toyama 3190 Gofuku, T oyama 930-8555 Japan

Abstract

AbstractBetuphenone 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.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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