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Enantioselective Total Synthesis of (+)-Sieboldine A

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journal contribution
posted on 20.01.2017, 00:00 by Mohammed K. Abd El-Gaber, Shigeo Yasuda, Eisuke Iida, Chisato Mukai
The first total synthesis of (+)-sieboldine A was completed starting from 5-(p-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 cis-hydrindane core with a quaternary carbon center. The late-stage Schmidt glycosylation led to the formation of the N-hydroxyazacyclononane ring.