title: A new synthetic approach to the polycyclic polyprenylated acylphloroglucinols.
abstract: [reaction: see text] The three-carbon alpha,alpha'-annulation of a sterically hindered cyclic beta-keto ester can be achieved by alkynylation with 3,3-diethoxypropyne, syn reduction of the alkyne with Co(2)(CO)(8) and Et(3)SiH, and an intramolecular aldol reaction. The method is potentially useful for the synthesis of nemorosone, hyperforin, and other polycyclic polyprenylated acylphloroglucinols.
authors: Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506-0055, USA.
authors: Roxana
authors: R
authors: Ciochina
authors: Robert B
authors: RB
authors: Grossman
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds; D003500:Cyclization; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000480:Alkynes; D001577:Benzophenones; D001643:Bridged Bicyclo Compounds; D013729:Terpenes; C437463:nemorosone; D010696:Phloroglucinol; C001654:hyperforin