title: Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.
abstract: The enantioselective syntheses of 10-hydroxylycopodine, deacetylpaniculine, and paniculine have been accomplished through use of a common intermediate. Key steps in the synthetic sequence toward these lycopodium alkaloids include formation of the tricyclic core via a conformationally accelerated, intramolecular Mannich cyclization and an organocatalyzed, intramolecular Michael addition to form the C(7)-C(12) linkage.
authors: Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331, United States.
authors: Mrinmoy
authors: M
authors: Saha
authors: Rich G
authors: RG
authors: Carter
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C581765:10-hydroxylycopodine; D000470:Alkaloids; D011807:Quinolizines; C581766:deacetylpaniculine; C581767:paniculine
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