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

✍ Scribed by George S Zaponakis; Haralambos E Katerinopoulos

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 83 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01260-6

✦ Synopsis

2R,3S)-2-[(1S)-3-(Benzyloxy)-1-(tert-butyldimethylsilyloxymethyl

)propyl]-3-phenylhexahydropyridine-a key synthetic intermediate 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.