Total syntheses of (Sp)-(+)- and (Rp)-(−)-spiniferin-1, a pair of unusual natural products with planar chirality

Abstract

(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 β-H elimination of allylic alcohol derivatives were considered as the key steps of these divergent syntheses.