Title

Elaboration of an Enzymatically-Derived Chiral Fragment via Olefin Cross Metathesis: A Novel Strategy for the Synthesis of Polyhydroxylated Pyrrolidines Chris Finlayson, Andrew Pace, and Kathryn Watts

Document Type

Article

Publication Date

2005

Abstract

Anisomycin, a biologically important pyrrolidine, was formally synthesized using a strategy incorporating the enantioselectivity of oxynitrilase, the power of olefin cross metathesis, and the rich chemistry of palladium pi-allyls. Overall, this coupled methodology afforded a strategic anisomycin intermediate in excellent chemical and optical yields (>95% ee). An olefin cross-metathesis reaction between an enzyme-derived chiral fragment and other functionalized alkenes extends the versatility of oxynitrilase in synthesis.

Advisor

Donald R. Deardorff

Department

chem

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