A novel synthesis of hexahydroapoerysopine dimethyl ether (11), by photolytic intramolecular arylation of the 6′-iodo- and 7-bromo-derivatives of 1,2,3,3a,4,5-hexahydro-N-(3,4-dimethoxyphenethyl)indol-6-one (6) and (8) to 2,3-dihydroapoerysopin-1(3aH)-one (9), followed by reduction with LiAlH4 to cis-2,3,3a,12c-tetrahydroapoerysopine (10) and then hydrogenation, is reported.
H. Iida, T. Takarai and C. Kibayashi, J. Chem. Soc., Chem. Commun., 1977, 644 DOI: 10.1039/C39770000644
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