An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach
The synthesis of enantiomerically enriched 7- and 8-hydroxy-stearic acids (7- and 8-HSA) has been successfully accomplished starting from chiral nonracemic 1-pentadecen-4-ol and 1-tetradecen-4-ol, respectively. Their Yamaguchi's esterification with 4-pentenoic and 5-hexenoic acids, respectively...
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ftunibolognairis:oai:cris.unibo.it:11585/545159 2024-04-14T08:03:04+00:00 An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach BOGA, CARLA MICHELETTI, GABRIELE Drioli, S Forzato, C Nitti, P. Prati, F. Boga, C. Drioli, S Forzato, C Micheletti, G. Nitti, P. Prati, F. 2016 STAMPA http://hdl.handle.net/11585/545159 https://doi.org/10.1055/s-0035-1561570 eng eng info:eu-repo/semantics/altIdentifier/wos/WOS:000376689000009 volume:27 issue:9 firstpage:1354 lastpage:1358 numberofpages:5 journal:SYNLETT http://hdl.handle.net/11585/545159 doi:10.1055/s-0035-1561570 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-84958824569 cross metathesi homoallylic alcohol hydroxystearic acid kinetic enzymatic resolution lipase B from Candida antarctica ring closing metathesis info:eu-repo/semantics/article 2016 ftunibolognairis https://doi.org/10.1055/s-0035-1561570 2024-03-21T17:36:13Z The synthesis of enantiomerically enriched 7- and 8-hydroxy-stearic acids (7- and 8-HSA) has been successfully accomplished starting from chiral nonracemic 1-pentadecen-4-ol and 1-tetradecen-4-ol, respectively. Their Yamaguchi's esterification with 4-pentenoic and 5-hexenoic acids, respectively, afforded the suitable dienic esters which were submitted to ring-closing metathesis reaction. After hydrogenation and basic hydrolysis of the complex reaction mixture, chiral nonracemic 7- and 8-HSA were obtained in about 40% total yield. Article in Journal/Newspaper Antarc* Antarctica IRIS Università degli Studi di Bologna (CRIS - Current Research Information System) Synlett 27 09 1354 1358 |
institution |
Open Polar |
collection |
IRIS Università degli Studi di Bologna (CRIS - Current Research Information System) |
op_collection_id |
ftunibolognairis |
language |
English |
topic |
cross metathesi homoallylic alcohol hydroxystearic acid kinetic enzymatic resolution lipase B from Candida antarctica ring closing metathesis |
spellingShingle |
cross metathesi homoallylic alcohol hydroxystearic acid kinetic enzymatic resolution lipase B from Candida antarctica ring closing metathesis BOGA, CARLA MICHELETTI, GABRIELE Drioli, S Forzato, C Nitti, P. Prati, F. An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach |
topic_facet |
cross metathesi homoallylic alcohol hydroxystearic acid kinetic enzymatic resolution lipase B from Candida antarctica ring closing metathesis |
description |
The synthesis of enantiomerically enriched 7- and 8-hydroxy-stearic acids (7- and 8-HSA) has been successfully accomplished starting from chiral nonracemic 1-pentadecen-4-ol and 1-tetradecen-4-ol, respectively. Their Yamaguchi's esterification with 4-pentenoic and 5-hexenoic acids, respectively, afforded the suitable dienic esters which were submitted to ring-closing metathesis reaction. After hydrogenation and basic hydrolysis of the complex reaction mixture, chiral nonracemic 7- and 8-HSA were obtained in about 40% total yield. |
author2 |
Boga, C. Drioli, S Forzato, C Micheletti, G. Nitti, P. Prati, F. |
format |
Article in Journal/Newspaper |
author |
BOGA, CARLA MICHELETTI, GABRIELE Drioli, S Forzato, C Nitti, P. Prati, F. |
author_facet |
BOGA, CARLA MICHELETTI, GABRIELE Drioli, S Forzato, C Nitti, P. Prati, F. |
author_sort |
BOGA, CARLA |
title |
An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach |
title_short |
An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach |
title_full |
An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach |
title_fullStr |
An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach |
title_full_unstemmed |
An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach |
title_sort |
easy route to enantiomerically enriched 7- and 8-hydroxy-stearic acids by olefin-metathesis-based approach |
publishDate |
2016 |
url |
http://hdl.handle.net/11585/545159 https://doi.org/10.1055/s-0035-1561570 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:000376689000009 volume:27 issue:9 firstpage:1354 lastpage:1358 numberofpages:5 journal:SYNLETT http://hdl.handle.net/11585/545159 doi:10.1055/s-0035-1561570 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-84958824569 |
op_doi |
https://doi.org/10.1055/s-0035-1561570 |
container_title |
Synlett |
container_volume |
27 |
container_issue |
09 |
container_start_page |
1354 |
op_container_end_page |
1358 |
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1796298120152219648 |