Access to Enantiopure 5‑, 7‑, and 5,7-Substituted cis- Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B

Pinto, AlexandreGriera Farres, RosaMolins i Grau, EliesFernández Cadenas, IsraelBosch Cartes, JoanAmat Tusón, Mercedes2017-05-262018-03-212017-03-211523-7060https://hdl.handle.net/2445/111625Stereoconvergent 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 cisdecahydroquinolines. 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.4 p.application/pdfeng(c) American Chemical Society , 2017AlcaloidesLactamesAlkaloidsLactamsAccess to Enantiopure 5‑, 7‑, and 5,7-Substituted cis- Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine Binfo:eu-repo/semantics/article6710542017-05-26info:eu-repo/semantics/openAccess28322567