10.1021/acs.orglett.6b03416.s002 Mohammed K. Abd El-Gaber Mohammed K. Abd El-Gaber Shigeo Yasuda Shigeo Yasuda Eisuke Iida Eisuke Iida Chisato Mukai Chisato Mukai Enantioselective Total Synthesis of (+)-Sieboldine A American Chemical Society 2017 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 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Enantioselective_Total_Synthesis_of_-Sieboldine_A/4633279 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.