192060-46-1Relevant academic research and scientific papers
Stellatolides, a new cyclodepsipeptide family from the sponge ecionemia acervus: Isolation, solid-phase total synthesis, and full structural assignment of stellatolide a
Martin, Maria Jesus,Rodriguez-Acebes, Raquel,Garcia-Ramos, Yésica,Martinez, Valentin,Murcia, Carmen,Digon, Isabel,Marco, Isabel,Pelay-Gimeno, Marta,Fernández, Rogelio,Reyes, Fernando,Francesch, Andrés M.,Munt, Simon,Tulla-Puche, Judit,Albericio, Fernando,Cuevas, Carmen
supporting information, p. 6754 - 6762 (2014/05/20)
The marine environment is a rich source of metabolites with potential therapeutic properties and applications for humans. Here we describe the first isolation, solid-phase total synthesis, and full structural assignment of a new class of cyclodepsipeptides from the Madagascan sponge Ecionemia acervus that shows in vitro cytotoxic activities at submicromolar concentrations. Seven structures belonging to a new family of compounds, given the general name stellatolides, were characterized. The sequence and stereochemistry of all the amino acids in these molecules were established by a combination of spectroscopic analysis, chemical degradation, and derivatization studies. Furthermore, the complete structure of stellatolide A was confirmed by an efficient solid-phase method for the first total synthesis and the full structural assignment of this molecule, including the asymmetric synthesis of the unique B-hydroxy acid moiety (Z)-3-hydroxy-6,8-dimethylnon-4-enoic acid.
Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: Proof of configurational assignment
Turk, Jeffrey A.,Visbal, Gonzalo S.,Lipton, Mark A.
, p. 7841 - 7844 (2007/10/03)
Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propion
Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones
Myers, Andrew G.,Yang, Bryant H.,Chen, Hou,McKinstry, Lydia,Kopecky, David J.,Gleason, James L.
, p. 6496 - 6511 (2007/10/03)
The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.
