155885-64-6Relevant articles and documents
New syntheses of the marine alkaloids eudistomins D and U
Rocca,Rocca, Patrick,Marsais,Marsais, Francis,Godard,Godard, Alain,Queguiner,Queguiner, Guy,Adams,Adams, Luqman,Alo,Alo, Babajide
, p. 7085 - 7088 (1995)
Short and convergent syntheses of eudistomins U and D are reported. The approach is based on a convergent methodology which involves such reactions as metalation and heteroring cross-coupling.
Manipulation of Water for Diversified Functionalization of Tetrahydro-β-carbolines (THβCs) with Indoles
Xu, Dekang,Ye, Fu,Ye, Jinxiang,Gao, Yu,Chen, Haijun
, p. 6160 - 6163 (2019)
Water plays a crucial role in organic synthesis. However, diversified functionalization manipulated by water is still rare and remains unexplored. Herein, we report the first water-manipulated protocol to achieve the diversified functionalization of tetrahydro-β-carbolines (THβCs) in an open flask at room temperature that exhibit a broad functional-group tolerance. More water leads to monoarylation, while less water leads to diarylation. Further one-step transformation afforded oxidized bis(indolyl)methanes, eudistomin U, and the related derivatives in satisfactory yields.
Efficient synthesis of eudistomin U and evaluation of its cytotoxicity
Roggero, Chad M.,Giulietti, Jennifer M.,Mulcahy, Seann P.
, p. 3549 - 3551 (2014)
Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis
Application of metal free aromatization to total synthesis of perlolyrin, flazin, eudistomin U and harmane
Santhanam, Srinath,Ramu, Abinaya,Baburaj, Baskar,Kalpatu Kuppusamy, Balasubramanian
, p. 2121 - 2127 (2020/03/04)
Application of our recently reported metal free reaction conditions to the total synthesis of the four different and selective biologically interesting β-carboline natural products is reported. Using this simple methodology, flazin, perlolyrine, eudistomin U and harmane containing heteroaryl and alkyl substituents at C1 position were synthesized in good yields. (Figure presented.).
Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines into β-carbolines under air
Zhao, Ziquan,Sun, Yan,Wang, Lilin,Chen, Xuan,Sun, Yanpei,Lin, Long,Tang, Yulin,Li, Fei,Chen, Dongyin
supporting information, p. 800 - 804 (2019/02/16)
Organic base DBN has been identified as an efficient reagent for promoting the dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines under air atmosphere, to access the corresponding β-carbolines in moderate to good yields. The utility of this protocol for the gram-scale synthesis of β-carboline alkaloids eudistomin U (7) and harmane (10) has also been demonstrated.