INVESTIGADORES
VARELA Oscar Jose
artículos
Título:
Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3-ones from arabinose.
Autor/es:
M. L. UHRIG & O. VARELA
Revista:
SYNTHESIS-STUTTGART
Editorial:
Thieme Chemistry
Referencias:
Lugar: Stuttgart; Año: 2005 p. 893 - 898
ISSN:
0039-7881
Resumen:
Abstract: Approaches to the enantioselective synthesis of the useful building blocks (2S)- and (2R)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the one-pot preparation of benzyl 2-O-acetyl-arabinopyranoside 3,4-thionocarbonates (7 and 14) from benzyl b-L- or b-D-arabinopyranosides (1 and 13). Trimethylphosphite-promoted olefination, followed by O-deacetylation and oxidation gave the optically pure enantiomeric enones 12 and 17 in about 50 % overall yield.
Key words: Enones, Carbohydrates, Stereoselective synthesis, Chiral pool, Olefination.
