4-hydroxylated piperidines and N-methyleuphococcinine (1-methyl-3-granatanone) from Picea (spruce) species. Identification and synthesis

Authors
Tawara, JN Lorenz, P Stermitz, FR
Citation
Jn. Tawara et al., 4-hydroxylated piperidines and N-methyleuphococcinine (1-methyl-3-granatanone) from Picea (spruce) species. Identification and synthesis, J NAT PROD, 62(2), 1999, pp. 321-323
Citations number
21
Categorie Soggetti
Agricultural Chemistry","Pharmacology & Toxicology
Journal title
JOURNAL OF NATURAL PRODUCTS
ISSN journal
01633864 → ACNP
Volume
62
Issue
2
Year of publication
1999
Pages
321 - 323
Database
ISI
SICI code
0163-3864(199902)62:2<321:4PAN(>2.0.ZU;2-A
Abstract
Three trace alkaloids from Colorado blue spruce, Picea pungens, were identi fied by synthesis and GCMS comparisons as 4 alpha-hydroxy-cis-2-methyl-6-(2 -oxopropyl)piperidine (1),4 alpha-hydroxy-cis-2-methyl-6-propylpiperidine ( 11), and 1-methylgranatanone (15) (N-methyl-9-aza-1-methylbicyclo[3.3.1]non ane or N-methyleuphococcinine). Alkaloids 1 and 11 are the first among nume rous known pine and spruce piperidines to contain a ring-oxygenated substit uent.