Access to Enantiopure 5-, 7-, and 5,7-Substituted cis-Decahydroquinolines: Enantioselective Synthesis of (-)-Cermizine B.
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.
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
Alexandre
A
Pinto
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
Rosa
R
Griera
Institut de Ciència de Materials de Barcelona (ICMAB, CSIC) , Campus UAB, 08193-Bellaterra, Spain.
Elies
E
Molins
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad Complutense de Madrid , 28040-Madrid, Spain.
Israel
0000-0002-0186-9774
I
Fernández
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
Joan
J
Bosch
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
Mercedes
0000-0002-9551-4690
M
Amat