Abstract:
Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). Copyright (C) 2000 Elsevier Science Ltd.
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Citas:
---------- APA ----------
Zunszain, P.A. & Varela, O.
(2000)
. Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone. Tetrahedron Asymmetry, 11(3), 765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6---------- CHICAGO ----------
Zunszain, P.A., Varela, O.
"Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone"
. Tetrahedron Asymmetry 11, no. 3
(2000) : 765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6---------- MLA ----------
Zunszain, P.A., Varela, O.
"Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone"
. Tetrahedron Asymmetry, vol. 11, no. 3, 2000, pp. 765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6---------- VANCOUVER ----------
Zunszain, P.A., Varela, O. Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone. Tetrahedron Asymmetry. 2000;11(3):765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6