First total synthesis of paracaseolide A.
The first total synthesis of the paracaseolide A, a very unusual tetraquinane oxa-cage bislactone recently isolated from the mangrove Sonneratia paracaseolaris, has been achieved. The final step and culmination of the eight-step synthetic sequence is a [4 + 2] dimerization of a 4-hydroxybutenolide, generated by singlet oxygen-mediated oxidation of a furan precursor.
Department of Chemistry, University of Crete , Vasilika Vouton, 71003 Iraklion, Crete, Greece.
Dimitris
D
Noutsias
Georgios
G
Vassilikogiannakis
D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry*; D019281:Dimerization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D026082:Singlet Oxygen; D013237:Stereoisomerism
C569208:paracaseolide A; D026082:Singlet Oxygen; D015107:4-Butyrolactone