652157-27-2Relevant academic research and scientific papers
Total synthesis of the Marine cyclic depsipeptide viequeamide A
Wang, Dongyu,Song, Shanshan,Tian, Ye,Xu, Youjun,Miao, Zehong,Zhang, Ao
supporting information, p. 974 - 978 (2013/07/05)
The first total synthesis of viequeamide A, a natural cyclic depsipeptide isolated from a marine button cyanobacterium, was achieved with the N-Me-Val-Thr peptide bond as the final macrocyclization site. The synthetic product gave nearly identical spectroscopic data to that reported for the natural product.
Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate
Nunnery, Joshawna K.,Suyama, Takashi L.,Linington, Roger G.,Gerwick, William H.
supporting information; experimental part, p. 2929 - 2932 (2011/06/23)
An efficient synthetic methodology for 3-hydroxy-2,2-dimethyloctynoic acid (DHOYA) and several variants, which are increasingly common fragments encountered in bioactive marine cyanobacterial metabolites, was developed. These fragments were obtained in three steps via a tertiary aldol reaction utilizing an Evans' chiral auxiliary to afford the desired stereochemistry at the β-hydroxy carbon. Thus far, this methodology has been successfully applied in determination of the absolute stereochemistry of eight cyanobacterial natural products, including the VGSC activator palymramide A.
Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines
May, Aaron E.,Willoughby, Patrick H.,Hoye, Thomas R.
, p. 3292 - 3294 (2008/09/20)
(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.
