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Paper | Regular issue | Vol 26, No. 3, 1987, pp.713-720
Published online, 1st January, 1970
DOI: 10.3987/R-1987-03-0713
Synthesis of a Reduced Neoproaporphine

Leon Mandell, Carol Anne Wilson, Shenna Sinclair, and Frederick Joseph Heldrich

*Department of Chemistry, Emory University, 1521 Pierce Drive Atlanta, Georgia 30322, U.S.A.


Hydrolysis of the Birch reduction pmduct from a 1-benzyltetrahydroisoquinoline, 8, affords a novel reduced neoproaporphine skeleton, 16. The formation of 16 is believed to proceed by initial formation of an intermediate bis-enone, 5, followed by an intramolecular Michael addition.