Studies on antianaphylactic agents—III

Publisher Summary Interest in studying the effects of structural modification of the naturally occurring steroid hormones upon activity has been evident ever since the elucidation of the structure of the sex hormones in the early 1930s. Emphasis on this particular field of steroid research was the result, first, of a natural curiosity to determine the chemical features essential for the complex hormonal activities of androgens, estrogens, and progestagens, and, secondly, of the very practical consideration of obtaining more desirable agents at lower cost for use in both human and veterinary medicine. Some of the features considered desirable for this purpose were, and still are, peroral effectiveness, high potency, extended duration of action, the separation of anabolic from androgenic and of gonadotropininhibiting from estrogenic activity. It soon became evident that, with the exception of the estrogens, the steroidal sex hormones are highly specific in their dependence of activity upon structure, and that only a limited number of structural variations would result in the retention of any biological activity, not to speak of increases in potency or separation of the physiological components involved.

Synthetic derivatives of cortical hormones.

Earlier evidence led to the view that in bimolecular olefin-forming eliminations the anti steric course is generally preferred over the syn. Recent experiments, however, show that in some common bimolecular elimination reactions, notably those involving onium bases, syn- and anti-eliminations proceed side by side, the former preferentially leading to the trans- and the latter to the cis-olefins.

The syn and anti Steric Course in Bimolecular Olefin‐Forming Eliminations

Dem von SEIDEL & STOLL aus bulgarischem Rosenol und seither auch aus Geraniumol isolierten linksdrehenden Monoterpenoxyd C10H18O wird auf Grund spektroskopischer und synthetischer Untersuchungen die Konstitution des (4 R)-cis-2-(2′-Methyl-l′-propenyl)-4-methyl-tetrahydropyrans (II) zuerteilt.

Zur Kenntnis des Rosenöls. 2. Mitteilung. Die Konstitution des Oxyds C10H18O aus bulgarischem Rosenöl

Altere Befunde fuhrten zur Ansicht, bei bimolekularen olefin-bildenden Eliminierungen sei die Abspaltung aus anti-Stellung generell gunstiger als die Abspaltung aus syn-Stellung. Nach neueren Untersuchungen kommen jedoch haufig, insbesondere wenn onium-Verbindungen als Substrate dienen, syn- und anti-koplanare Eliminierungen nebeneinander zum Zuge. Dabei fuhrt dann im Normalfall der syn-Weg uberwiegend zum trans-, der anti-Weg uberwiegend zum cis-Olefin.

R. P. Holysz

Papers

Preparation and Dehydrohalogenation of 4-Halo-3-ketosteroids