A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone.
Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.
Stark
Lucy M
LM
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Pekari
Klaus
K
Sorensen
Erik J
EJ
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D015394:Molecular Structure; D010879:Piperazines; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D001578:Benzopyrans; D010879:Piperazines; C103033:harziphilone; C007306:triethylenediamine