4538-50-5Relevant articles and documents
Synthesis of (±)-eusynstyelamide A
Barykina, Olga V.,Snider, Barry B.
, p. 2664 - 2667 (2010)
The synthesis of (±)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the α-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.
Synthesis of the fungal macrolide berkeleylactone A and its inhibition of microbial biofilm formation
Schobert, Rainer,Schrey, Hedda,Schriefer, Manuel G.,Stadler, Marc,Zeng, Haoxuan
, p. 4743 - 4751 (2021/06/11)
The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a β-ketoester to install the stereogenic centres. A domino addition-Wittig olefination of a 13-hydroxytetradecanal intermediate with the cumulated ylide Ph3PCCO closed the macrocyle by establishing the α,β-unsaturated ester group, necessary for the attachment of the sidechain thiol via a thia-Michael reaction. The synthetic berkeleylactone A inhibited the formation of Staphylococcus aureus biofilms and showed significant dispersive effects on preformed biofilms of Candida albicans by at least 45% relative to untreated controls at concentrations as low as 1.3 μg mL-1.
Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides
Liang, Jian,Soucie, Luke N.,Blechschmidt, Daniel R.,Yoder, Aaron,Gustafson, Addie,Liu, Yu
supporting information, p. 513 - 518 (2019/01/14)
Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.
The asymmetric total synthesis of (+)-salvianolic acid A
Zheng, Yong,Song, Wei-Bin,Xuan, Li-Jiang
supporting information, p. 5047 - 5050 (2016/07/25)
An asymmetric synthesis of (+)-salvianolic acid A with cardioprotective properties, has been accomplished in a convergent manner in eight steps and 10.6% overall yield. This synthesis features an asymmetric addition of organometallics to optically pure 2,3-epoxypropionate in the presence of BF3·Et2O, Ru(III)-catalyzed directed [Formula presented] olefination, and I2-catalyzed isomerization reaction.
