The synthesis of enantiomerically enriched 7- and 8-hydroxystearic acids (7- and 8-HSA) has been successfully accomplished starting from chiral non racemic 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 non racemic 7- and 8-HSA were obtained in about 40% total yield.

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

DRIOLI, Sara;FORZATO, Cristina;NITTI, PATRIZIA;
2016

Abstract

The synthesis of enantiomerically enriched 7- and 8-hydroxystearic acids (7- and 8-HSA) has been successfully accomplished starting from chiral non racemic 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 non racemic 7- and 8-HSA were obtained in about 40% total yield.
https://www.thieme-connect.de/DOI/DOI?10.1055/s-0035-1561570
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11368/2877783
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