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

Department of Chemistry, Columbia University, New York, New York, United States
Angewandte Chemie International Edition (Impact Factor: 11.26). 02/2007; 46(9):1451-4. DOI: 10.1002/anie.200604308
Source: PubMed


(Chemical Equation Presented) 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).

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