A new synthetic approach to the polycyclic polyprenylated acylphloroglucinols.
[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.
Ciochina
Roxana
R
Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506-0055, USA.
Grossman
Robert B
RB
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
D000480:Alkynes; D001577:Benzophenones; D001643:Bridged Bicyclo Compounds; D013729:Terpenes; C437463:nemorosone; D010696:Phloroglucinol; C001654:hyperforin