Steroide und Sexualhormone 254. Mitteilung [1] Synthetische Versuche in der Limonin‐Reihe III. Stereospezifische Alkoxy‐ und Dialkoxy‐Alkylierungen von 19‐Hydroxy‐testosteronacetat

Three different procedures for intramolecular alkoxy‐alkylation of 19‐hydroxy‐testosterone‐acetate ( 4 ) are described each yielding a mixture of two products monoalkylated either at position C(2), C( 4 ) or C(6). In all cases the alkoxy groups are introduced stereospecifically from the β‐side. Treatment of 4 with I 2 /(CH 3 ) 2 CO leads to 5 and 6. Reaction of 4 with HgCl 2 /ClCH 2 SCH 3 gives rise to 12 and 13 whereas treatment with HC(OCH 3 ) 3 /CH 3 C 6 H 4 SO 3 H affords 15 , 16 and 17 .