Ring-closing metathesis (RCM) has developed into a powerful method for synthesis of a large assortment of carbo- and hetero-cyclic rings.  One critical problem, which persists in many applications of this important reaction class, is the lack of control of Z- or E-selectivity, particularly in cases where there is little or no energetic difference between the two isomers (kinetic as well as thermodynamic control not feasible).  We have developed a series of molybdenum and tungsten complexes designed for efficient control of Z-selectivity in olefin metathesis.  Through the use of these new complexes, we have succeeded in achieving a highly stereoselective total synthesis of a natural product through catalytic Z-selective RCM; previous attempts involving the use of other catalyst classes affords little or no selectivity.

<i>Z</i>-selective ring-closing metathesis reactions: Application to a stereoselective total synthesis of a natural product

242nd National Meeting (2011)

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Z-selective ring-closing metathesis reactions: Application to a stereoselective total synthesis of a natural product