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Access To Enantiopure 5-, 7-, And 5,7-Substituted Cis-Decahydroquinolines: Enantioselective Synthesis Of (-)-Cermizine B.

A. Pinto, R. Griera, E. Molins, I. Fernández, J. Bosch, M. Amat
Published 2017 · Chemistry, Medicine

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Stereoconvergent cyclocondensation reactions of (R)- or (S)-phenylglycinol with appropriately substituted cyclohexanone-based δ-keto esters are the key steps of short synthetic routes to enantiopure 5-, 7-, and 5,7-substituted cis-decahydroquinolines. The factors governing the stereoselectivity of the cyclocondensation are discussed. The potential of the methodology is illustrated by a protecting-group-free synthesis of the phlegmarine-type Lycopodium alkaloid (-)-cermizine B.
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