Alkene Metathesis in Organic Synthesis by Alois Fuerstner

By Alois Fuerstner

Content material: Olefin metathesis by means of well-defined complexes of molybdenum and tungsten / R.R.Schrock -- Ruthenium-catalyzed metathesis reactions in natural synthesis / A. Furstner -- Ring-closing metathesis within the synthesis of epothilones and polyether traditional items / K.C. Nicolaou, N.P. King, Y. He -- Catalytic ring-closing metathesis and the improvement of enantioselective methods / A.H. Hoveyda -- Enyne metathesis / M. Mori -- Cross-metathesis / Susan E. Gibson, S.P. willing -- fresh advances in ADMET chemistry / D. Tindall, J.H. Pawlow and K.B. Wagener -- Bioactive polymers / L.L. Kiessling, L.E. robust

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38 A. Fürstner 5 Selected Applications of RCM to Target Oriented Synthesis . . . 6 Carbocyclic Nucleosides . . . . . . . . . . Manzamine A . . . . . . . . . . . . . Epothilone A . . . . . . . . . . . . . (+)-Lasiodiplodin . . . . . . . . . . . Tricolorin A . . . . . . . . . . . . . (-)-Gloeosporone: Development of a Binary Metathesis Catalyst System . . . . . . . . . .

Zation (ROMP) of cycloalkenes with 8–11 ring atoms, is a highly favored process due to the release of ring strain [1]. Despite this seemingly adverse situation, a rapidly growing number of successful applications indicates that even medium sized rings can be prepared by RCM in moderate to excellent yields (Tables 1, 4) [29]. It is likely that the entropy gained upon dissecting one diene into two olefins together with the evaporative loss of ethylene (cf. Scheme 4) can compensate for the unfavorable increase in enthalpy during the cyclization process.

38 2 Synthesis, Structure, Mechanism and Activity of Ruthenium-Based Metathesis Catalysts . . . . . . . . 3 Ruthenium Carbene Complexes and General Aspects of RCM . . Ruthenium Allenylidene Complexes . . . . . . . . . Less Defined Ruthenium Catalysts . . . . . . . . . . 39 43 46 3 The Application Profile of the Standard Ruthenium-Based Metathesis Catalysts in Synthesis . . . . . . . . . . 5 Effects of Olefin Substitution . . . . . Functional Group Compatibility .

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