Synthesis of the spirocyclic core of the prunolides using a singlet oxygen-mediated cascade sequence.
[reaction: see text] A highly efficient and rapid four-step synthesis of the bis-spiroketal core of the prunolide natural products, starting from furan itself, is described. The key step and culmination of the synthesis, responsible for zipping up the spirocyclic core, is a singlet oxygen-orchestrated cascade sequence in which a double photooxygenation of a 1,2-difuryl alkene precursor precedes dehydration and spirocyclization to furnish the intact prunolide core.
Sofikiti
Nikoletta
N
Department of Chemistry, University of Crete, 71409 Iraklion, Crete, Greece.
Tofi
Maria
M
Montagnon
Tamsyn
T
Vassilikogiannakis
Georgios
G
Stratakis
Manolis
M
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis*; D015394:Molecular Structure; D026082:Singlet Oxygen / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*
D005663:Furans; D008387:Marine Toxins; D013141:Spiro Compounds; C508396:prunolide A; C508397:prunolide B; C508398:prunolide C; C508395:rubrolide A; D026082:Singlet Oxygen