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Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition
1Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16801, USA.
Organic Letters
|May 12, 2001
Abstract:
[reaction: see text]. The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.