Recommanded Product: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Chirality transfer in an Ireland-Claisen rearrangement: a new approach toward the Iboga alkaloids. Author is Hoeck, Stefan; Koch, Florian; Borschberg, Hans-Juerg.
The synthesis of the isoquinuclidine core of the Iboga alkaloid family is described. This building block contains the entire stereochem. information of the targeted natural products. Starting with (S)-4-(hydroxymethyl)-4-butanolide, a derivative available in two steps from l-glutamate, (S)-4-benzyloxy-5,5-dimethoxypentanoic acid was obtained in four steps. Mitsunobu esterification with (S)-but-3-en-2-ol furnished the inverted ester I, which was then subjected to an Ireland-Claisen rearrangement. This crucial step took place with a very satisfactory chirality transfer from the alc. component to the new carbon backbone of the product II. After transformation of the resulting silyl ester function into a hydroxylamino group, the di-Me acetal moiety was hydrolyzed with 3 M sulfuric acid at 47 °C. Under these conditions, the resulting cyclic nitrone could not be isolated, because it underwent a rapid intramol. nitrone-olefin [3+2]-cycloaddition reaction to furnish the expected tricyclic isoxazolidine derivative III in 67% yield. After chromatog. purification, this product was obtained enantiomerically pure and with a chem. purity of 96%. The targeted isoquinuclidine building block III was thus obtained from (S)-4-(hydroxymethyl)-4-butanolide in 13 steps with an overall yield of 9.2%, which amounts to an average yield of 83.3% per step.
This compound((S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one)Recommanded Product: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.
Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI