Divergent synthesis of the co-isolated mycotoxins longianone, isopatulin, and (Z)-ascladiol via furan oxidation.
Longianone and the biosynthetically related mycotoxins isopatulin and (Z)-ascladiol were prepared following a divergent route from a readily available furan diol. The route toward longianone features an unprecedented TBAF-promoted intramolecular oxa-Michael reaction to a conjugated keto enoate, and the oxidation of dihydrolongianone to longianone with stabilized IBX. The route to isopatulin features a chemoenzymatic synthesis of (Z)-ascladiol, and the regioselective oxidation of (Z)-ascladiol to isopatulin with MnO(2).
Lykakis
Ioannis N
IN
Department of Chemistry, University of Crete, Voutes 71003, Iraklion, Greece.
Zaravinos
Ioannis-Panayotis
IP
Raptis
Christos
C
Stratakis
Manolis
M
D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D005663:Furans; D006574:Heterocyclic Compounds, 2-Ring; D007783:Lactones; D009183:Mycotoxins; D013141:Spiro Compounds; C552376:longianone; C038422:ascladiol; C552375:isopatulin; C039281:furan