97294-60-5Relevant academic research and scientific papers
Divergent Total Syntheses of (-)-Crinipellins Facilitated by a HAT-Initiated Dowd-Beckwith Rearrangement
Chen, Ruyi,Ding, Hanfeng,Hu, Jialei,Xie, Hujun,Xiong, Fengping,Zhao, Yifan
supporting information, p. 2495 - 2500 (2022/02/16)
A hydrogen atom transfer (HAT)-initiated Dowd-Beckwith rearrangement reaction was developed, which enables the efficient assembly of diversely functionalized polyquinane frameworks. By incorporation of an iridium-catalyzed regio- and enantioselective hydrogenation and a diastereocontrolled ODI-[5+2] cycloaddition/pinacol rearrangement cascade reaction, the asymmetric total syntheses of eight tetraquinane natural products, including (-)-crinipellins A-F and (-)-dihydrocrinipellins A and B, have been achieved in a concise and divergent manner.
Total Syntheses of Crinipellins Enabled by Cobalt-Mediated and Palladium-Catalyzed Intramolecular Pauson–Khand Reactions
Huang, Zhihui,Huang, Jun,Qu, Yongzheng,Zhang, Weibin,Gong, Jianxian,Yang, Zhen
, p. 8744 - 8748 (2018/07/14)
Efficient total syntheses of the naturally occurring, potent antibiotic compounds (?)-crinipellin A and (?)-crinipellin B are described. The key advanced intermediate, a fully functionalized tetraquinane core, was constructed by a novel thiourea/palladium-catalyzed Pauson–Khand reaction. This intermediate can serve as a common intermediate for the collective total synthesis of other members of the crinipellin family.
Total synthesis of (-)-crinipellin A
Kang, Taek,Song, Seog Boem,Kim, Won-Yeob,Kim, Byung Gyu,Lee, Hee-Yoon
, p. 10274 - 10276 (2014/08/05)
The first total synthesis of (-)-crinipellin A is described. The tetraquinane core skeleton of crinipellin A was assembled through the tandem [2 + 3] cycloaddition reaction of an allenyl diazo substrate containing a cyclopentane ring in a single operation. The absolute stereochemistry was confirmed through the total synthesis.
