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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Bibliographic Details
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
Description
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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