73763-45-8Relevant academic research and scientific papers
Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties
Laville, Rmi,Nguyen, Thanh Binh,Moriou, Cline,Petek, Sylvain,Debitus, Ccile,Al-Mourabit, Ali
, p. 1351 - 1366 (2015)
Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.
Total Synthesis of the Proposed Microcyclamides MZ602 and MZ568
Liu, Yi,Zhao, Xiangyun,Wang, Hongbo,Liu, Huili,Sui, Zhuyin,Yan, Bingfei,Du, Yuguo
, p. 1065 - 1073 (2020/12/21)
The first convergent total synthesis for the proposed structures of microcyclamides MZ602 (1) and MZ568 (2) has been accomplished in 11 linear steps with 12.5 and 16.8% overall yield, respectively. Key features of the syntheses include a one-pot cascade r
Total synthesis of wewakazole B
Long, Bohua,Zhang, Jingzhao,Tang, Xudong,Wu, Zhengzhi
supporting information, p. 9712 - 9715 (2016/10/31)
Wewakazole B is a novel cyclodecapeptide with highly potent cytotoxic activity isolated from a sample of M. producens collected from the Red Sea. It contains nine common and three modified amino acid residues. The first total synthesis of Wewakazole B was successfully achieved on a gram scale, unambiguously confirming its structure. Notable features include the careful choice of amino acid-protecting groups and the construction of three different substituted oxazoles present in this natural product.
Synthesis and electrochemical behaviour of β-halodehydroamino acid derivatives
Ferreira, Paula M. T.,Monteiro,Pereira
experimental part, p. 499 - 513 (2010/11/04)
Several new β,β-dihalo and β-halo-β-substituted dehydroalanines and dehydrodipeptides were synthesized by reacting the corresponding dehydroamino acid derivative with a N-halosuccinimide or in the case of β,β-di-iododehydroalanines with iodine. The results obtained confirmed that the stereochemical outcome of the halogenation reaction with β-substituted dehydroamino acids depends on the substrate. Thus, an increase Z-stereoselectivity was found when the β-phenyldehydroalanines were used as substrates and when these compounds were N-protected with 4-tolylsulfonyl or with carbamates. From this study, it is also possible to conclude that when N-iodosuccinimide was used as reagent a much higher Z-stereoselectivity is found. The electrochemical behaviour of the halogenated dehydroamino acids was studied by cyclic voltammetry. The results show a shift in the reduction peak to higher potentials of the β-halogenated dehydroamino acids when compared with the corresponding non-halogenated derivatives. As expected, the β,β-dihalodehydroalanines exhibit higher peak potentials than β-halo-β-substituted dehydroalanines and the bromo derivatives have lower peak potentials when compared with the corresponding iododehydroamino acids. Controlled potential electrolysis of several β-halo-β-substituted dehydroamino acids afforded the corresponding dehalogenated dehydroamino acids as mixtures of their E and Z-isomers. In all cases, the major isomer isolated results from dehalogenation without isomerization. These new results show that electrochemical reduction constitutes a valuable method for the synthesis of the E-isomer of β-substituted dehydroalanines. Springer-Verlag 2010.
