Enantioselective Total Synthesis of (+)-Sieboldine A
Open Access
- 2 January 2017
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 19 (2) , 320-323
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.Keywords
Funding Information
- Japan Society for the Promotion of Science (15H02490, 15K18826)
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