acetogenins has been researched along with murisolin* in 3 studies
3 other study(ies) available for acetogenins and murisolin
| Article | Year |
|---|---|
Transannular O-heterocyclization: a useful tool for the total synthesis of Murisolin and 16,19-cis-Murisolin.
Transannular O-heterocyclization is applied as a key step in a total synthesis. This highly stereoselective and metal-free transformation introduces four stereocenters in one step. It was chosen to be the pivotal step in the synthesis of Murisolin and 16,19-cis-Murisolin, two annonaceous acetogenins. The efficiency of this synthesis is further illustrated by a stereodivergent late-stage separation of both synthetic routes. Topics: Acetogenins; Candida; Cyclization; Furans; Lactones; Lipase; Molecular Structure; Stereoisomerism | 2012 |
Solution-phase parallel synthesis with oligoethylene glycol sorting tags. Preparation of all four stereoisomers of the hydroxybutenolide fragment of murisolin and related acetogenins.
The principles of the oligoethylene glycol (OEG) mixture synthesis are illustrated with the synthesis of all four possible stereoisomers of a hydroxybutenolide fragment common to murisolin and many other acetogenins. Modified dimethoxybenzyl groups with varying numbers of OEG units (-CH2CH2O-) are used to protect alcohols and serve as codes for configurations at two stereocenters. The encoded isomers are carried through several steps in a sequence of mixing prior to the reaction and then demixing during the separation to give individual pure products. A new tagging scheme is introduced in which a stereocenter bearing a hydroxy group is given two different tags. These initially redundant tags then serve to encode the configuration of another (untagged) stereocenter by appropriate pairwise reactions of the tagged precursors. The experimental features (reaction, analysis, separation, and characterization) of OEG mixture synthesis are detailed and are compared to and contrasted with those of fluorous mixture synthesis. Topics: 4-Butyrolactone; Acetogenins; Ethylene Glycols; Fatty Alcohols; Furans; Lactones; Magnetic Resonance Spectroscopy; Stereoisomerism | 2006 |
On the proof and disproof of natural product stereostructures: characterization and analysis of a twenty-eight member stereoisomer library of murisolins and their Mosher ester derivatives.
Characterizing a stereoisomer library of 28 of the 64 possible isomers of the acetogenin murisolin, including 24 of the 32 possible diastereomers, provides a complete picture of the spectra of this class of molecules. Remarkably, each of the 32 diastereomers exhibits one of only six sets of substantially identical (1)H NMR spectra under standard conditions. These spectra follow directly from a local symmetry analysis of the dihydroxy-THF fragment of the molecule and provide no information about the configuration about the hydroxybutenolide. Eighteen tris-Mosher ester derivatives of library members have been made, and their spectra were analyzed to give a complete picture of the usefulness of chiral derivatives. The tris-Mosher esters of the 64 isomers of murisolin will exhibit 40 sets of spectra: 16 isomers have unique spectra whereas 24 isomers share an identical spectrum with one other isomer. This identity occurs even though the pairs of compounds were already diastereomers (not enantiomers) before the derivatization. The complete set of spectra allows any murisolin or closely related compound to be narrowed to one or two structures by simple matching and without recourse to assignment and subtraction of resonances. The structure of murisolin was proved to be the 4R,15R,16R,19R,20R,34S isomer, whereas the assignment of 16,19-cis-murisolin as RRRSSS was changed to the RSSRRS diastereomer and murisolin A is suggested to be RSRRRS. Topics: Acetogenins; Biological Products; Combinatorial Chemistry Techniques; Esters; Fatty Alcohols; Furans; Lactones; Molecular Conformation; Molecular Structure | 2006 |