Enantioselective Total Synthesis of (+)-Sieboldine A

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• 作者：Mohammed K. Abd El-Gaber ; Shigeo Yasuda ; Eisuke Iida ; Chisato Mukai
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：19
• 期：2
• 页码：320-323
• 全文大小：393K
• ISSN：1523-7052

文摘

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.