Scalable Protecting-Group-Free Total Synthesis of Resibufogenin and Bufalin DOI

Shao‐Peng Yu,

Q.‐E. ZHANG,

Xueqing Zhong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9704 - 9709

Published: Nov. 4, 2024

A chemoenzymatic synthesis access to resibufogenin and bufalin was developed in seven steps without protecting groups. Starting with androstenedione (AD), an α-OH introduced directly at C14 by hydroxylase P-450lun, which further used as the directing group for hydrogenation fully control C17 configuration β-orientation after Suzuki cross-coupling. Dehydration of 14α-OH followed epoxidation delivered resibufogenin. Simultaneously, also obtained via a challenging anaerobic Mukaiyama hydration.

Language: Английский

Synthesis of Bufadienolide Cinobufagin via Late-Stage Singlet Oxygen Oxidation/Rearrangement Approach DOI

Colin Tichvon,

Ievgen M. Zviagin,

Zoey Surma

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2445 - 2450

Published: March 15, 2024

This manuscript describes a concise synthesis of cinobufagin, natural steroid the bufadienolide family, from readily available dehydroepiandrosterone (DHEA), as well its α5-epimer derived 3-

Language: Английский

Citations

4
Plants’ Impact on the Human Brain—Exploring the Neuroprotective and Neurotoxic Potential of Plants DOI Creative Commons

Georgiana Moise,

Alex-Robert Jîjie, Elena-Alina Moacă

et al.

Pharmaceuticals, Journal Year: 2024, Volume and Issue: 17(10), P. 1339 - 1339

Published: Oct. 7, 2024

Plants have long been recognized for their potential to influence neurological health, with both neuroprotective and neurotoxic properties. This review explores the dual nature of plant-derived compounds impact on human brain.

Language: Английский

Citations

3
Cinobufagin: Unveiling the hidden bufadienolide’s promise in combating alimentary canal cancer development and progression – a comprehensive review DOI
Beatriz Leme Boaro, Enzo Pereira de Lima, Durvanei Augusto Maria

et al.

Naunyn-Schmiedeberg s Archives of Pharmacology, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

Language: Английский

Citations

0
Scalable Protecting-Group-Free Total Synthesis of Resibufogenin and Bufalin DOI

Shao‐Peng Yu,

Q.‐E. ZHANG,

Xueqing Zhong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9704 - 9709

Published: Nov. 4, 2024

A chemoenzymatic synthesis access to resibufogenin and bufalin was developed in seven steps without protecting groups. Starting with androstenedione (AD), an α-OH introduced directly at C14 by hydroxylase P-450lun, which further used as the directing group for hydrogenation fully control C17 configuration β-orientation after Suzuki cross-coupling. Dehydration of 14α-OH followed epoxidation delivered resibufogenin. Simultaneously, also obtained via a challenging anaerobic Mukaiyama hydration.

Language: Английский

Citations

2