Summary
A novel synthesis of 8-methylisoquino[2,1-b][2,7]naphthyridinium salts7 is reported using the intramolecular cyclization of the 1-substituted isoquinolines5 as the key step, which in turn are obtained by alkylation of theReissert compounds1. The salts7 can be reduced by NaBH4 yielding the 8α- and 8β-methylstereomers (±)-alamaridine and (±)-epi-alamaridine9c and11c, respectively.
Similar content being viewed by others
Literatur
3. Mitt.: Reimann E., Benend Ht. (1993) Arch. Pharm.327, im Druck
Renz H. (1994) Dissertation, München
Reimann E., Renz H. (1993) Arch. Pharm.326: 253
Reimann E., Benend Ht. (1992) Monatsh. Chem.123: 939
Jahangir, MacLean D. B., Holland H. L. (1987) Can. J. Chem.65: 727
Bhattacharya A., Mukhopadhyay R., Sinha R. R., Ali E., Pakrashi S. C. (1988) Tetrahedron44: 3477
Bobbit J. M., Scola D. A. (1969) J. Org. Chem.25: 560
Rey A. W., Szarek W. A., MacLean D. B. (1992) Can. J. Chem.70: 2992
Webb J. L., Corwin A. H. (1944) J. Am. Chem. Soc.66: 1456
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Reimann, E., Renz, H. Protoberberine ausReissert-Verbindungen, 4. Mitt. Eine neue Synthese des (±)-Alamaridins und des (±)-epi-Alamaridins. Monatsh Chem 125, 1397–1406 (1994). https://doi.org/10.1007/BF00811089
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00811089