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.
Poly(Alkyl Glycidate Carbonate)s as Degradable Pressure-Sensitive Adhesives
Beharaj, Anjeza,Ekladious, Iriny,Grinstaff, Mark W.
supporting information, p. 1407 - 1411 (2019/01/14)
Insertion of CO2 into the polyacrylate backbone, forming poly(carbonate) analogues, provides an environmentally friendly and biocompatible alternative. The synthesis of five poly(carbonate) analogues of poly(methyl acrylate), poly(ethyl acrylate), and poly(butyl acrylate) is described. The polymers are prepared using the salen cobalt(III) complex catalyzed copolymerization of CO2 and a derivatized oxirane. All the carbonate analogues possess higher glass-transition temperatures (Tg=32 to ?5 °C) than alkyl acrylates (Tg=10 to ?50 °C), however, the carbonate analogues (Td≈230 °C) undergo thermal decomposition at lower temperatures than their acrylate counterparts (Td≈380 °C). The poly(alkyl carbonates) exhibit compositional-dependent adhesivity. The poly(carbonate) analogues degrade into glycerol, alcohol, and CO2 in a time- and pH-dependent manner with the rate of degradation accelerated at higher pH conditions, in contrast to poly(acrylate)s.
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.
