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...
Published in: | Synlett |
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Main Authors: | , , , , , |
Other Authors: | , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2016
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Subjects: | |
Online Access: | http://hdl.handle.net/11585/545159 https://doi.org/10.1055/s-0035-1561570 |
Summary: | 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. |
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