An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach

• Published in: Synlett
• Main Authors: Boga, Carla, Drioli, Sara, Forzato, Cristina, Micheletti, Gabriele, Nitti, Patrizia, PRATI, Fabio
• Other Authors: Prati, Fabio
• Format: Article in Journal/Newspaper
• Language: English
• Published: country:STUTTGART 2016
• Subjects: cross metathesi; homoallylic alcohol; hydroxystearic acid; kinetic enzymatic resolution; lipase B from Candida antarctica; ring closing metathesi; Organic Chemistry; Antarc*; Antarctica
• Online Access: http://hdl.handle.net/11380/1133332; https://doi.org/10.1055/s-0035-1561570; http://www.thieme-connect.com/ejournals/toc/synlett

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.