Enantioselective Total Synthesis of (+)-Sieboldine A
Mohammed K Abd El-Gaber1, Shigeo Yasuda1, Eisuke Iida1
1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
Abstract:
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.
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