Totally synthetic plus or minus-13-alkyl-3-hydroxy and methoxy-gona-135 (10)-trien-17-ones and related compounds.

A series of gona-135(10)-triene derivatives were synthesized with various substituents at C-13 and variations in ring D size. The substituents at C-13 were ethyl n-propyl isopropyl n-butyl isobutyl isoamyl n-hexadecyl groups; at C-3 were hydroxyl or methoxyl; D rings were 5 or 6 membered. The key reaction in synthesis is a Michael condensation of a vinyl ketone followed by cyclodehydration at C 9-10 and C 8-11. Biologic activity was reported for 3 of the derivatives the ketal decanoic ester and ketone.