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- W2022048009 abstract "Reaction of (20S)-5α-chloro-3β-hydroxypregnane-20-carboxaldehyde (9, prepared in two steps from stigmasterol) with oxygen and potassium tert-butoxide, followed by trimethyl phosphite treatment, afforded 5α-chloro-3β,17α-dihydroxypregnan-20-one (6) and 3β,17α-dihydroxypregn-5-en-20-one (7). This mixture was converted into 7 by potassium hydroxide treatment, and into 17α-hydroxypregn-4-ene-3,20-dione (8) by reaction with pyridinium dichromate followed by potassium hydroxide treatment. Bromination-dehydrobromination of 9, in one or two steps, afforded (Z)- and (E)-5α-chloro-3β-hydroxypregn-17(20)-ene-20-carboxaldehyde (11). Reaction of 11 with oxygen and potassium hydroxide gave 5α-chloro-3β-hydroxypregn-16-en-20-one (12), which was converted to 3β-hydroxypregna-15,6-dien-20-one (13) by further potassium hydroxide treatment, and to pregna-4,16-diene-3,20-dione (14) by Oppenauer reaction using excess aluminium isopropoxide. Einfache Umwandlung eines Pregnan-20-carboxaldehyds in 17α-Hydroxypregnan-20-one und Pregn-16-en-20-one Umsetzung von (20S)-5α-Chlor-3β-hydroxypregnan-20-carboxaldehyd (9, dargestellt in zwei Stufen aus Stigmasterin) mit Sauerstoff und Kalium-tert-butylat sowie anschließend mit Trimethylphosphit lieferte 5α-Chlor-3β,17α-dihydroxypregnan-20-on (6) und 3β, 17α-Dihydroxypregn-5-en-20-on (7). Diese Mischung wurde durch Kaliumhydroxid in 7 übergeführt, während Reaktion mit Pyridinium-dichromat und danach mit Kaliumhydroxid 17α-Hydroxypregn-4-en-3,20-dion (8) ergab. Bromierung-Dehydrobromierung von 9 in einer oder zwei Stufen ergab (Z)- und (E)-5α-Chlor-3β-hydroxypregn-17(20)-en-20-carboxaldehyd (11). Dessen Reaktion mit Sauerstoff und Kaliumhydroxid lieferte 5α-Chlor-3β-hydroxypregn-16-en-20-on (12). Letzteres wurde durch weitere Kaliumhydroxid-Behandlung in 3β-Hydroxypregna-5,16 dien-20-on (13) und mittels Oppenauer-Reaktion, unter Anwendung von überschüssigem Aluminiumisopropylat, in Pregna-4,16-dien-3,20-dion (14) übergeführt." @default.
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- W2022048009 date "1982-10-18" @default.
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- W2022048009 title "A Ready Conversion of a Pregnane-20-carboxaldehyde to 17α-Hydroxypregnan-20-ones and Pregn-16-en-20-ones" @default.
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- W2022048009 doi "https://doi.org/10.1002/jlac.198219821007" @default.
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