A Spectral Method for the Determination of the Position of a Phenolic Group on Ring A of an Aporphine. Four New Aporphines From Polyalthia acuminata

Journal of Natural Products
1982.0

Abstract

Polyalthia acuminata Thw. (Annonaceae) has furnished the new aporphines (−)-norliridinine (1), (−)-3-hydroxynornuciferine (2), (−)-norannuradhapurine (9), and (−)-noroliveroline (11). Monophenolic aporphines bearing the phenol group at C-3 exhibit both a bathochromic shift as well as hyperchromic effect in their uv spectra in basic solution. N-Methylation of 1 yields (−)-liridinine, which is thus firmly represented by expression 7. Similar treatment of 2 leads to (−)-3-hydroxynuciferine (8) which is identical with the alkaloid (−)-lirinine. This last transformation establishes with certainty the position of the phenol in (−)-lirinine. © 1982, American Chemical Society. All rights reserved.

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