Spiniferin-1, a rare planar chiral natural product with a 1,6-methano[10]annulene skeleton, has been synthesized via a novel polyfluoroalkanosulfonyl fluoride induced cascade carbocation rearrangement reaction. Natural spiniferin-1 was established as a racemic mixture by comparing its specific rotation with those of our synthesized S p -(+)-spiniferin-1 and its R p -(-)-enantiomer.

C-or O-benzylation of 1,3-dicarbonyl compounds is one of the most fundamental methodologies for carbon-carbon or carbon-oxygen bond formation in organic synthesis. Perfluoroalkanosulfonyl fluoride (R f SO 2

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Lewis acid catalyzed mercaptolysis of steroidal SapogeninS was reinvestigated. Besides obtaining the reported 26-thioacetals 5 under milder conditions, a new type of compounds Am(a)-furostena26-thioethers 6 were also synthesized through the mercaptolysis of steroidal sapogenins, which can be used to the synthesis of the steroidal molecule with side chains.