Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element

Article abstract of DOI:10.1002/anie.200601358

(Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.