Total Synthesis of Peribysin E Necessitates Revision of the Assignment of its Absolute Configuration

Abstract

The right way round: Peribysin E, a naturally occurring adhesion inhibitor, has been synthesized and, as a result, its absolute configuration reassigned. The natural and nonnatural enantiomers can be reached starting from (R)- or (S)-carvone, respectively. A key step is the ring contraction of 1 to 2 (see scheme, TBS=tert-butyldimethylsilyl, TES=triethylsilyl).