John F. Poletto

The formation of steroid enolate anions by reductive procedures: The synthesis of 17-alkylprogesterones

Abstract Treatment of a 16-dehydro, 17-acetoxy, 17-hydroxy or 17-bromopregn-20-one with a liquid ammonia solution of lithium, barium or calcium (and in at least one instance sodium) afforded an intermediate 17-enolate anion, which on reaction with the appropriate alkyl, allyl and benzyl halide furnished the corresponding 17-alkyl, allyl and benzyl-pregn-20-one. A very useful liquid-liquid partition column chromatographic procedure is described.

Prostaglandins and congeners VIII. An improved procedure for the conjugate addition of 3-oxy-E-1-alkenyl ligands via lithium alanate reagents. 11-deoxyprostaglandin E1 analogues☆

1-Jod-E-1-octen-3-ol (Ia) liefert die beiden O-Tritylather (Ib) und (Ic), die mit Butyllithium und Trimethylaluminium zu (IIb) und (IIc) metalliert werden.

6-Substituted-6-dehydro-17-alkylprogesterones: Highly active oral progestins

The preparation of a series of 6-chloro-6-dehydro-17-alkylprogesterones, of the 6-fluoro and 6-methyl derivatives of 6-dehydro-17-ethylprogesterone and of 6-chloro-1,6-bisdehydroprogesterone is described. The oral progestational activity of these and other 17-alkyl-progesterone derivatives is discussed.

A Convenient Procedure for the Sulfation of Flavonoid Glycosides: Preparation of Rotin Nona- and Deca Sulfates

Abstract A satisfactory procedure for the sulfation of flavonoid glycosides is described and is illustrated by the preparation of rutin nona and deca sulfates. Compounds of this type are important modulators of the complement part of the immune system.