A new route to the prostaglandin skeleton via radical alkylation. Synthesis of 6-oxoprostaglandin E1

T Toru, Y Yamada, T Ueno, E Maekawa…

Index: Toru, Takeshi; Yamada, Yoshio; Ueno, Toshio; Maekawa, Eturo; Ueno, Yoshio Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4815 - 4817

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Citation Number: 27

Abstract

Abstract: A new, mild, and efficient method for the construction of the prostanoid skeleton involving cuprate addition to a-(pheny1seleno) 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 E,, a biologically active and naturally occurring compound.

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