Abd El-Gaber, Mohammed K. Yasuda, Shigeo Iida, Eisuke Mukai, Chisato Enantioselective Total Synthesis of (+)-Sieboldine A The first total synthesis of (+)-sieboldine A was completed starting from 5-(<i>p</i>-methoxybenzyloxy)­pentyne in 19 steps. The enantioselective Keck allylation provided the dienyne derivative, which was exposed to the Pauson–Khand conditions to afford the bicyclo[4.3.0]­nonenone derivative with high stereoselectivity with an ee value of 93%. The following Ueno–Stork reaction formed the <i>cis</i>-hydrindane core with a quaternary carbon center. The late-stage Schmidt glycosylation led to the formation of the <i>N</i>-hydroxyazacyclononane ring. Enantioselective;19 steps;ci;bicyclo;synthesis;hydrindane core;hydroxyazacyclononane ring;Sieboldine;dienyne;late-stage Schmidt glycosylation;Synthesi;quaternary carbon center;Ueno;Pauson;formation;stereoselectivity;sieboldine;enantioselective Keck allylation;methoxybenzyloxy;ee value 2017-01-20
    https://acs.figshare.com/articles/dataset/Enantioselective_Total_Synthesis_of_-Sieboldine_A/4633279
10.1021/acs.orglett.6b03416.s002