Synthetic studies towards the octahydro-1H-benzo[f]pyrrolo[3,2,1-ij]quinolines: enantioselective synthesis of (2R,3S)-2-[(1S)-3-(benzyloxy)-1-(tert-butyldimethyl-silyloxymethyl)propyl]-3-phenylhexahydropyridine
作者:George S Zaponakis、Haralambos E Katerinopoulos
DOI:10.1016/s0040-4039(01)01260-6
日期:2001.9
for the preparation of (6aS,11bS,11cS)-1H-benzo[f]pyrrolo[3,2,1-ij]quinoline—was synthesized in nine steps. The synthetic approach uses both enantiomers of the chiral auxiliary trans-2,5-bis(methoxymethoxymethyl)pyrrolidine, employed in different stages of the synthesis for the construction of two out of the three stereogenic centers in the above mentioned intermediate.
(2 R,3 S)-2-[(1 S)-3-(苯甲氧基)-1-(叔丁基二甲基甲硅烷基氧甲基)丙基] -3-苯基六氢吡啶-(6 a S,11b S的关键合成中间体通过9个步骤合成了,11c S)-1 H-苯并[ f ]吡咯并[3,2,1- ij ]喹啉。合成方法使用手性辅助反式-2,5-双(甲氧基甲氧基甲基)吡咯烷的两种对映异构体,它们在合成的不同阶段用于在上述中间体中的三个立体异构中心中的两个构建。