1192033-72-9Relevant academic research and scientific papers
Catalytic asymmetric synthesis of key intermediate for scytophycin C
Cui, Jin,Watanabe, Takumi,Shibasaki, Masakatsu
, p. 446 - 448 (2016)
We achieved a formal total synthesis of scytophycin C. The synthesis demonstrates the utility of the catalytic asymmetric direct thioamide-aldol reaction for the preparation of polyketide structures, and was accomplished via diastereoselective allylation,
Total synthesis and stereochemical assignment of (-)-ushikulide A
Trost, Barry M.,O'Boyle, Brendan M.,Hund, Daniel
supporting information; experimental part, p. 15061 - 15074 (2010/01/30)
We report the determination of the full stereostructure of (-)-ushikulide A (1), a spiroketal containing macrolide by total synthesis. Ushikulide A (1) was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC50 = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin (2), a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallography. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asymmetric alkynylation of a simple saturated aldehyde with methyl propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochemical assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.
Formal total synthesis of N-methylmaysenine
Wang, Lin,Gong, Jianxian,Deng, Lujiang,Xiang, Zheng,Chen, Zhixing,Wang, Yuefan,Chen, Jiahua,Yang, Zhen
supporting information; experimental part, p. 1809 - 1812 (2009/09/06)
A novel synthetic approach for the formal total synthesis of N-methylmaysenine (1) has been developed. Key steps Involve the Ti-mediated vlnylogous Mukaiyama aldol reaction of chlral ketene silyl N,O-acetal with β-dithiane-substituted aldehyde, an aldol c
