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Schlatter, Hans‐Rudolf; Lüthy, Christoph; Graf, Walter

Steroide und Sexualhormone 255. Mitteilung [1]. Synthetische Versuche in der Limonin‐Reihe IV Eine neuartige Westphalen‐Lettré‐Umlagerung in der 4,4‐Dimethyl‐Steroid‐Reihe

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  • Media type: E-Article
  • Title: Steroide und Sexualhormone 255. Mitteilung [1]. Synthetische Versuche in der Limonin‐Reihe IV Eine neuartige Westphalen‐Lettré‐Umlagerung in der 4,4‐Dimethyl‐Steroid‐Reihe
  • Contributor: Schlatter, Hans‐Rudolf; Lüthy, Christoph; Graf, Walter
  • imprint: Wiley, 1975
  • Published in: Helvetica Chimica Acta
  • Language: English
  • DOI: 10.1002/hlca.19750580512
  • ISSN: 0018-019X; 1522-2675
  • Keywords: Inorganic Chemistry ; Organic Chemistry ; Physical and Theoretical Chemistry ; Drug Discovery ; Biochemistry ; Catalysis
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>Applying the HgCl<jats:sub>2</jats:sub>/ClCH<jats:sub>2</jats:sub>SCH<jats:sub>3</jats:sub>‐reaction 1. to 4,4‐dimethyl‐Δ<jats:sup>5</jats:sup>‐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<jats:sup>5</jats:sup>‐androstene (12) with HgCl<jats:sub>2</jats:sub>/ClCH<jats:sub>2</jats:sub>SCH<jats:sub>3</jats:sub>‐reagent (→13). Reaction of 3β, 17β‐diacetoxy‐4,4‐dimethyl‐19‐(methoxymethyl)‐Δ<jats:sup>5</jats:sup>‐androstene (7) with hydrogenfluoride/urea‐reagent gives rise to a similar rearranged product (→15).</jats:p>