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  • Title: 4-hydroxylated piperidines and N-methyleuphococcinine (1-methyl-3-granatanone) from Picea (Spruce) species. Identification and synthesis.
    Author: Tawara JN, Lorenz P, Stermitz FR.
    Journal: J Nat Prod; 1999 Feb; 62(2):321-3. PubMed ID: 10075774.
    Abstract:
    Three trace alkaloids from Colorado blue spruce, Picea pungens, were identified by synthesis and GC-MS comparisons as 4alpha-hydroxy-cis-2-methyl-6-(2-oxopropyl)piperidine (1), 4alpha-hydroxy-cis-2-methyl-6-propylpiperidine (11), and 1-methylgranatanone (15) (N-methyl-9-aza-1-methylbicyclo[3.3. 1]nonane or N-methyleuphococcinine). Alkaloids 1 and 11 are the first among numerous known pine and spruce piperidines to contain a ring-oxygenated substituent.
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