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;
2016-01-01
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.File in questo prodotto:
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