Synthesis of macrocyclic scaffolds suitable for diversity-oriented synthesis of macrolides |
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Authors: | Michael E Grimwood |
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Institution: | Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta T2N 1N4, Canada |
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Abstract: | Synthesis of macrocyclic glycal-based scaffolds for diversity-oriented synthesis was studied and demonstrated using macrocyclic enyne ring-closing metathesis. The roles of ring size, alkyne substitution, and orientation relative to the glycal were studied. In all cases, the cyclization showed preference for the thermodynamically favored endo-mode of closure and a trans-double bond at the ring-closure site, leaving macrocyclic scaffolds all containing multiple orthogonal functional groups available for further diversification. |
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