Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition.
[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.
Maeng
J H
JH
Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16801, USA.
Funk
R L
RL
D000171:Acrolein / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*
D004146:Dioxanes; C098358:FR 901483; D007166:Immunosuppressive Agents; D009943:Organophosphorus Compounds; D000171:Acrolein; C059814:4-dioxanone