Steroids. CLXXXVII.¹ Transannular Reactions at Saturated Carbon Atoms. Part 2.² C-19 Oxygenation³

Hormones

“…Albert Bowers (1930Bowers ( -1990 [46,47] at Syntex observed for secondary steroidal alcohols, that these are amenable to cyclisation with lead tetraacetate, supposed the stereochemistry in the δ-position is adequate. The key step is a radical 1,5-H-abstraction, which is intrinsically more favourable than a 1,4-or 1,6-abstraction.…”

19‐nor‐Steroide V. Neue Synthese von 6‐Dehydro‐19‐nor‐Steroiden. Über Steroide, 208. Mitteilung

“…5,6 [13] 5,75,5,80 (Schulter),6,01,6,15,6,28,8,15,9,55. 9,65,10,40 und 2,74,5,75,5,81 (Schulter),6,00,6,15,6,29,7,27,7,35,8,16,8,95,9,42 und 11,38 p. UV. 2,75, 5,77, 6,01, 6,17, 6,30, 7,37,8,20,8,60,9,42 und 11,38p.…”

“…2,75, 5,77, 6,01, 6,17, 6,30, 7,37,8,20,8,60,9,42 und 11,38p. UV.-Spektrum: A, , , 5,83 (Schulter),6,00,6,15,6,26,7,27,7,35,8,15,8,96,9,57,10,35 und 11,40 p. UV.-Spektrum: A , , , = 288 nm (E = 21700).…”

“…2,84,5,75,5,78 (Schulter),5,85 (Schulter),6,00,6,15,6,27,7,35,8,60,8,97,9,56,10,35 und 11,40 Banden ma. bei 5,75, 5,79, 8,05, 8,25, 9,15, 9,25, 9,57 und 1,155).…”

“…5,77, 5,82, 6.01, 6,17, 6,30, 8,19, 8,26, 8.35, 9,56, 10 5,76, 6,00, 6,16, 6,30, 8,30, 8,55, 955, 10,31 und 5,75, 5,81, 6,00, 6,15, 6,26, 8,14, 9,00, 9,24., 9,55, 9,75, 9,85 und 3, 77-Dioxo-19-hydroxy-A4~B-androstadien ( X I I ) : 22,s g rohes Acetat X I wurden in 1000 ml Banden u.a. bei 2,75, 5,75, 6,01, 6,12, 6,30, 7,35, 8,20, 8,27, 9,48 und 5,74,G,OO,6,18,6.25,8,15,9,28,9,90 2,68, 2,85, 5,73, 5,86, 6,00, 6,15, 6,26, 8,14, 8,26, 9,19, 9,60, 9,90 und 11.40 5,74, 6,01, 6,16, 6,30, 7,52, 8,21, 9,58, 9,95, 10,31, 10,83 und 5,74, 5,79, 7,25, 7,43, 8,50, 9,34, 9,60 und 9,95 (7,25 g) bei 120-122" schmolz. Die reine Verbindung (nach Umkristallisieren aus wenig Methanol) schmilzt bei 122-125".…”