Synthons for Syntheses of Spiroheptane Analogues of Prostaglandins

Article abstract of DOI:10.1007/BF00799169

Methods for the preparation of synthons for syntheses of spiro<2.4>heptane analogues of prostaglandins are described.Two of them (1a and 1b) enable the syntheses of 11-deoxy-type compounds and were prepared from spiro<2.4>heptan-4-one (3) which after transformation into the 5-phenylthio-α, β-unsaturated ketone 5 was subjected to conjugate addition of organocuprate reagent 6.The third synthon (2) - a potential intermediate in syntheses of complete spiro<2.4>heptane analogues of prostaglandins-was prepared from the bicyclic ketone 10 by Baeyer-Villiger oxidation follo wed by epoxidation. - Keywords: Prostaglandin analogues; Spiro<2.4>heptan-4-ones; 2H-Cyclopentafuran-2-ones; Desulfurization; Conjugate addition of cuprate