Total synthesis of
potent cell-adhesion inhibitors peribysins A
and B has been accomplished for the first time in racemic form. A
Diels–Alder/aldol sequence to build the skeleton and decoration
of the desired functionalities of the targeted natural products using
highly stereoselective operations are the highlights. The structures
of synthesized peribysins were fully characterized using spectral
data and single-crystal X-ray analysis. Through this total synthesis,
the initially proposed structure of peribysin B has been revised.
Furthermore, the cell-adhesion inhibition potential of the scaffold
(two peribysins + three analogues) was confirmed using anti-adhesion
assay.