A preliminary approach to nonenolizable beta,beta-tricarbonyls: assembly of a hyperevolutin prototype.
A synthetic approach to the hyperevolutin A acylated phloroglucinol ring system is described. Thus, intramolecular allene-nitrile oxide cycloaddition of 10 was used to construct the bicyclic framework and vicinal quaternary centers in cycloadduct 20 in the key bond-forming step. Treatment of 20 with Raney nickel and hydrogen gas produced primary enamine 21 which contains a nonenolizable beta,beta-tricarbonyl group in latent form.
Young
David G J
DG
Department of Chemistry, University of Tennessee, Knoxville, Knoxville, Tennessee 37996, USA. dgjyoung@utk.edu
Zeng
Dongxiang
D
D000218:Adamantane / Q000031:analogs & derivatives / Q000138:chemical synthesis; D001685:Biological Factors / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds; D002384:Catalysis; D028084:Clusiaceae / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D001685:Biological Factors; D001643:Bridged Bicyclo Compounds; D013729:Terpenes; C106690:garsubellin A; C464481:hyperevolutiin A; C409384:sampsonione J; D010696:Phloroglucinol; D000218:Adamantane; C001654:hyperforin