Journal of the Chemical Society. Perkin transactions I p. 715 - 718 (1996)
Update date:2022-08-04
Topics:
Kawanaka, Yasufumi
Ono, Naoya
Yoshida, Yukio
Okamoto, Sentaro
Sato, Fumie
Starting with commercially available (3S,4R)-3-(methoxymethyloxy)-2-methylidene-4-siloxycyclopentanone 2, useful 6-keto-prostaglandin intermediates 1 have been prepared in good yields by a sequence of reactions which includes treatment with NaBr in the presence of BF3·OEt2, Pd-catalysed coupling of the resulting 2-bromomethyl-4-siloxycyclopent-2-enone 3 with the alkenylborane 4 or 9 and conversion of the alkenyl moiety into an epoxy and then into a keto group. The synthesis of 6-keto-PGE1, ornoprostil and Δ2-trans-6-keto-PGE1 by using 1 is also described.
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