Total syntheses of (S-p)-(+)- and (R-p)-(-)-spiniferin-1, a pair of unusual natural products with planar chirality

(S-p)-(+)-Spiniferin-1 and (R-p)-(-)-spiniferin-1, a pair of unusual marine natural products with planar chirality, were firstly synthesized via a polyfluoroalkanosulfonyl fluoride induced homoallylic carbocation rearrangement reaction. The chiral resolution and palladium-catalyzed beta-H elimination of allylic alcohol derivatives were considered as the key steps of these divergent syntheses.