TY - JOUR T1 - Formal enantioselective synthesis of (-)-epiquinamide by proline-catalyzed one-pot sequential -amination/propargylation of aldehyde and asymmetric dihydroxylation of olefin JF - Synlett Y1 - 2016 A1 - Ahuja, Brij Bhushan A1 - Emmanuvel, Lourdusamy A1 - Sudalai, Arumugam KW - Amination KW - diastereoselective KW - Dihydroxylation KW - Proline KW - quinolizidine AB -

Two independent routes to the formal synthesis of (-)-epiquinamide, have been described: the first route utilizes an l-proline-catalyzed one-pot sequential -amination/propargylation of aldehyde, while the second one employs asymmetric dihydroxylation as the key reaction to install the stereochemistry. While the first synthesis was accomplished in nine steps with 24.4% overall yield and dr 9:1, the second strategy resulted in the synthesis in eight steps with 36.4% overall yield and with perfect enantiocontrol.

PB - GEORG THIEME VERLAG KG CY - RUDIGERSTR 14, D-70469 STUTTGART, GERMANY VL - 27 IS - 11 U3 -

Foreign

U4 - 2.323 ER -