Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone
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 appr...
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todo:paper_09574166_v11_n3_p765_Zunszain2023-10-03T15:52:22Z Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone Zunszain, P.A. Varela, O. lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09574166_v11_n3_p765_Zunszain |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity |
| spellingShingle |
lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity Zunszain, P.A. Varela, O. Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| topic_facet |
lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity |
| description |
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. |
| format |
JOUR |
| author |
Zunszain, P.A. Varela, O. |
| author_facet |
Zunszain, P.A. Varela, O. |
| author_sort |
Zunszain, P.A. |
| title |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_short |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_full |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_fullStr |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_full_unstemmed |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_sort |
two approaches to the enantioselective synthesis of (4r)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| url |
http://hdl.handle.net/20.500.12110/paper_09574166_v11_n3_p765_Zunszain |
| work_keys_str_mv |
AT zunszainpa twoapproachestotheenantioselectivesynthesisof4r4hydroxymethyl4thiobutyro14lactone AT varelao twoapproachestotheenantioselectivesynthesisof4r4hydroxymethyl4thiobutyro14lactone |
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