Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.
The asymmetric total synthesis of the polyprenylated acylphloroglucinol hyperibone K has been achieved using an enantioselective alkylative dearomatization-annulation process. NMR and computational studies were employed to probe the mode of action of a chiral phase-transfer (ion pair) catalyst.
Qi
Ji
J
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
Beeler
Aaron B
AB
Zhang
Qiang
Q
Porco
John A
JA
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D018360:Crystallography, X-Ray; D045782:Hemiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D045782:Hemiterpenes; C555113:hyperibone K; D010696:Phloroglucinol; D000218:Adamantane