Concise Total Synthesis of rac-Betuphenone F |
| |
| Authors: | Nguyen Ngoc Thanh Luan Dr Takuya Okada Dr Naoki Toyooka |
| |
| Institution: | 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: | 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-oxabicyclo3.3.1]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. |
| |
| Keywords: | anti-austerity anti-cancer betuphenone total synthesis 2-oxabicyclo[3 3 1]nonane |
|
|
