A New Route to the Prostaglandin Skeleton via Radical Alkylation. Synthesis of 6-Oxoprostaglandin E1

Article abstract of DOI:10.1021/ja00222a045

A new, mild, and efficient method for the construction of the prostanoid skeleton involving cuprate addition to α-(phenylseleno)cyclopentenones followed by radical-based coupling to the resulting products with allylstannane derivatives is described.The method is applied to the synthesis of 6-oxoprostaglandin E₁, a biologically active and naturally occurring compound.