BIOMAT Database Logo BIOMAT Database Logo

Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction. 2021

Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, Sichuan, China.

An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter.

UI MeSH Term Description Entries

Related Publications

Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Enantioselective Total Syntheses of (-)-20-epi-Vincamine and (-)-20-epi-Eburnamonine by Ir-Catalyzed Asymmetric Imine Hydrogenation/Lactamization Cascade.
August 2020, Chemistry (Weinheim an der Bergstrasse, Germany),
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Asymmetric synthesis of (-)-eburnamonine and (+)-epi-eburnamonine from (4S)-4-ethyl-4-[2-(hydroxycarbonyl)ethyl]-2-butyrolactone.
December 2001, The Journal of organic chemistry,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Synthesis of cyclohexylidenehydrazine-fused polycyclics via a photocatalytic radical cascade reaction of 2-ethynylaldehyde hydrazones.
February 2017, Chemical communications (Cambridge, England),
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Total synthesis of (-)-lycorine and (-)-2-epi-lycorine by asymmetric conjugate addition cascade.
April 2009, Organic letters,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Total Synthesis of Clerobungin A via a Cascade Cyclization Reaction.
December 2016, The Journal of organic chemistry,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Asymmetric Total Synthesis of (-)-Pavidolide B via a Thiyl-Radical-Mediated [3 + 2] Annulation Reaction.
December 2019, The Journal of organic chemistry,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Asymmetric Total Synthesis of C9'-epi-Sinefungin.
July 2020, Organic letters,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Enantioselective Total Synthesis of (-)-Caldaphnidine O via a Radical Cyclization Cascade.
August 2019, Journal of the American Chemical Society,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Asymmetric synthesis of CF3-containing tetrahydroquinoline via a thiourea-catalyzed cascade reaction.
May 2017, Organic & biomolecular chemistry,
Yuan Huang, and Fanglin Xue, and Hengmao Liu, and Fei Xue, and Xiao-Yu Liu, and Hao Song, and Yong Qin
Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso-Cyclization.
November 2020, Angewandte Chemie (International ed. in English),
Copied contents to your clipboard!