Short and stereoselective synthesis of α-methylene-β-hydroxy-γ-butyrolactone diastereomers : Structures revised by theoretical investigations

A short synthetic approach allowed the preparation, in two steps, of (3S,4R)- and (3R,4R)-2- methylene-3-hydroxy-4-(hydroxymethyl)-γ-butyrolactones from 2,3-O-(3-pentylidene)-D-glyceraldehyde, with overall yields of 32 % and 9 %, respectively. The structure of these γ-butyrolactones was revised by e...

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Autores principales: Díaz, Gaspar, Carvalho, Gláucia S., Soares, Flávia R. F., Alcântara, Antônio F. de C., Diaz, Marisa A. N.
Formato: Articulo Comunicacion
Lenguaje:Inglés
Publicado: 2011
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Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/8356
http://www.latamjpharm.org/resumenes/30/8/LAJOP_30_8_2_8.pdf
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Sumario:A short synthetic approach allowed the preparation, in two steps, of (3S,4R)- and (3R,4R)-2- methylene-3-hydroxy-4-(hydroxymethyl)-γ-butyrolactones from 2,3-O-(3-pentylidene)-D-glyceraldehyde, with overall yields of 32 % and 9 %, respectively. The structure of these γ-butyrolactones was revised by experimental and theoretical investigations.