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Steroide und Sexualhormone 255. Mitteilung [1]. Synthetische Versuche in der Limonin‐Reihe IV Eine neuartige Westphalen ‐ Lettr é‐Umlagerung in der 4,4‐Dimethyl‐Steroid‐Reihe
Author(s) -
Schlatter HansRudolf,
Lüthy Christoph,
Graf Walter
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580512
Subject(s) - chemistry , reagent , limonin , medicinal chemistry , stereochemistry , organic chemistry , chromatography
Abstract Applying the HgCl 2 /ClCH 2 SCH 3 ‐reaction 1. to 4,4‐dimethyl‐Δ 5 ‐7‐oxo‐19‐hydroxy‐androstene (9) one observes an intramolecular rearrangement of the «Westphalen‐Lettré»‐type (→11). A related rearrangement is observed by treating 3‐oxo‐4,4‐dimethyl‐17β‐acetoxy‐Δ 5 ‐androstene (12) with HgCl 2 /ClCH 2 SCH 3 ‐reagent (→13). Reaction of 3β, 17β‐diacetoxy‐4,4‐dimethyl‐19‐(methoxymethyl)‐Δ 5 ‐androstene (7) with hydrogenfluoride/urea‐reagent gives rise to a similar rearranged product (→15).