ABSTRACT
In connection with the synthesis of shwarone (II), a sesquiterpinoid with interesting pharmacological properties, some results on the alkylation in the 9-position of the model substance delta6-octalone-1 (VI) are reported. Methylation, especially if carried out in polar aprotic solvents, gives mainly the trans derivative, this being the type needed for synthesis of compound (II); alkylation with allylbromides and propargyl gives mainly the cis isomer.
Subject(s)
Antivenins/chemical synthesis , Sesquiterpenes/chemical synthesis , Alkylation , Chemistry, Pharmaceutical , Chromatography, Gas , Insecta , Isomerism , Methylation , Snake Venoms/antagonists & inhibitors , Spectrophotometry, InfraredABSTRACT
New approaches for the synthesis of cis, trans, trans, octadeca-9,11,13-trienoic acid (I) and its trans, trans, cis isomer (II), starting from the easily available propargyl alcohol are described.
Subject(s)
Fatty Acids, Unsaturated/chemical synthesis , Hydrolysis , Indicators and Reagents , Magnetic Resonance SpectroscopyABSTRACT
The preparation of 2-formyl-1.4-benzodioxane by reduction of the corresponding ethyl ester, and some reactions of this aldehyde carried out with the aim of obtaining new pharmacologically active derivatives, are described. Wittig reactions with stabilized, semi-stabilized, and reactive phosphoranes resulted in the formation of the 2-alkenyl derivatives. Reaction with a primary amine led to the corresponding imine. The 1.3-dithiane was also prepared and its behaviour with strong bases and alkylating reagents investigated.
