Gamma-spiroketal gamma-lactones from 2-(gamma-hydroxyalkyl)furans: syntheses of epi-pyrenolide D and crassalactone D.
Photooxygenation of 2-(gamma-hydroxyalkyl)furans followed by dehydration affords, in one synthetic operation and in high yield, gamma-spiroketal gamma-lactones. This newly developed technology was successfully applied to the synthesis of three different epimers of pyrenolide D, as well as to the first synthesis of the anticancer natural product crassalactone D and its C4-epimer.
Pavlakos
Elias
E
Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Iraklion, Crete, Greece.
Georgiou
Thomas
T
Tofi
Maria
M
Montagnon
Tamsyn
T
Vassilikogiannakis
Georgios
G
D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D005663:Furans; D006878:Hydroxides; D007783:Lactones; D013141:Spiro Compounds; C545739:crassalactone D; C545740:pyrenolide D; C520774:spiroketal; C031356:hydroxide ion; D006861:Hydrogen Peroxide