title: One-pot organocatalytic enantioselective domino double-Michael reaction and Pictet-Spengler-lactamization reaction. A facile entry to the "inside yohimbane" system with five contiguous stereogenic centers.
abstract: An expedited method was developed for the enantioselective synthesis of dodecahydrobenz[a]indolo[3,2-h]quinolizine containing five contiguous stereogenic centers with high enantioselectivities (>99% ee). The methodology comprises a domino organocatalytic double Michael reaction and Pictet-Spengler-lactamization reaction. The structures and absolute configurations of the appropriate products were confirmed by X-ray analysis.
authors: Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621 Taiwan, ROC. chebch@ccu.edu.tw
authors: Bor-Cherng
authors: BC
authors: Hong
authors: Wei-Kai
authors: WK
authors: Liao
authors: Nitin S
authors: NS
authors: Dange
authors: Ju-Hsiou
authors: JH
authors: Liao
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D011807:Quinolizines