Synthesis of new thio corticosteroids including 1α,9α-epidithio-11β,17α,21-trihydroxy-16β-methylpregn-4-ene-3,20-dione

On t h e Regioselectivity of SH-Containing Nucleophiles towards Androsta-l,4-diene-3,17-dione, a Precursor for Biologi-cally Active Steroids Thioketals have been prepared from androsta-1,4-diene-3,17-served by using the thiol3b leading to 5b. With the araliphatic dione (1) and SH-containing compounds in the presence of thiol 3f compound 5f is selectively formed. In contrast to the different catalysts. The thioketals 4 are obtained by using the described thioketal formation, the thiol 3 d yields in addition aromatic thiols 3 d , 3e, and 3g, whereas the aliphatic thiols to 4 d a double Michael addition product 7, which was pre3a and 3c yield a mixture of regioisomeric products 4-6. A dominantly obtained by using other catalysts and/or a higher higher selectivity with regard to the 17-0x0 group was ob-reaction temperature.Steroidketone wie Androsta-1,4-dien-3,17-dion (1) spielen sowohl im Laboratorium als auch bei technischen Synthesen eine wesentliche Rolle als Edukt-Molekule fur zahlreiche chemisch und biochemisch induzierte Strukturumwandlungen"]. Die bei Vorhandensein mehrerer funktioneller Gruppen auftretenden Probleme der Regioselektivitat gelten bei der GroBzahl von Steroiden als gelost; eine der Ausnahmen stellt allerdings 1 dar. Selbst durch ein geschicktes Abstimmen sowohl elektronischer als auch sterischer Effekte seitens des Reagenz ist man nur in wenigen Fallen in der Lage, Schlusselreaktionen schutzgruppenfrei und regioselektiv zu gestalten [2,31.

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Synthesis of new thio corticosteroids including 1α,9α-epidithio-11β,17α,21-trihydroxy-16β-methylpregn-4-ene-3,20-dione

Cited by 2 publications

References 8 publications

ChemInform Abstract: Synthesis of New Thio Corticosteroids Including 1α,9α‐ Epidithio‐11β,17α,21‐trihydroxy‐16β‐methylpregn‐4‐ene‐ 3,20‐dione.

ChemInform Abstract: Synthesis of New Thio Corticosteroids Including 1α,9α‐ Epidithio‐11β,17α,21‐trihydroxy‐16β‐methylpregn‐4‐ene‐ 3,20‐dione.

Zur Regioselektivität SH‐haltiger Nucleophile gegenüber Androsta‐1,4‐dien‐3,17‐dion, einem Vorläufer für biologisch aktive Steroide

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