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.
Boga, C., Drioli, S., Forzato, C., Micheletti, G., Nitti, P., Prati, F. (2016). An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach. SYNLETT, 27(9), 1354-1358 [10.1055/s-0035-1561570].
An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy-stearic Acids by Olefin-Metathesis-Based Approach
BOGA, CARLA;MICHELETTI, GABRIELE;
2016
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
