Pa. Marchand et al., OXYGEN INSERTION IN SESAMUM-INDICUM FURANOFURAN LIGNANS - DIASTEREOSELECTIVE SYNTHESES OF ENZYME-SUBSTRATE ANALOGS, Canadian journal of chemistry, 75(6), 1997, pp. 840-849
The furofuran lignans in sesame seed have an unusual oxygen insertion
between their furan and aryl rings. In our continuing investigations o
n the isolation and characterization of the enzyme(s) involved, the di
astereoselective syntheses of various substrate analogues for the oxyg
en insertion step were developed for future substrate specificity and
inhibitor studies. This synthetic strategy also provided entry to so-c
alled furofuranone epoxy-lignans, such as salicifoliol from Bupleurum
sp., and acuminatolide from Helichrysum sp.