über die Herstellung von 17α‐Oxy‐20‐keto‐Steroiden aus 17(20)‐En‐20‐acetamino‐Steroiden

Chemistry of N-bromamines and N-chloramines

“…Representative of these preparations are (1) treatment of a solution of alkylamine and sodium bicarbonate with chlorine to form the alkyldichloramine,4 4 (2) use of -butyl hypochlorite with an amine which leads to the corresponding N-chloro derivative,11•46-47 and (3) the interaction of an amine with N-chlorosuccinimide. 48 A novel method involves the cleavage of trimethylsilylamines with chlorine gas (eq 3);49 yields range from 40 to 90 %. N-Bromoand N-iododialkylamines R2NSiRs + Cl, -> R,NC1 + RsSiCl (3) were also prepared in this fashion.…”

“…Ind. (Milan), 48,264 (1966); Chem. Abstr., 64, 19360 (1966). (155) F. Minisci, R. Galli, A. Galli, and R. Bernardi, Chim.…”

“…Ind, (Milan), 48, 845 (1966); Chem. Abstr., 65, 15289 (1966). (160) F. Minisci, V. Trabucchi, and R. Galli, ibid., 48,716 (1966); Chem. Abstr., 66, 10785 (1967). (161) F. Minisci and R. Galli, Tetrahedron Lett., 2531 (1966).…”

Synthesis of (+)-Mearsine

“…with substitution of acetaldehyde for formaldehyde in the first step (Mannich reaction), to accommodate the methyl group at position 3 in 1, and use of 5-methyl-2-cyclohexenone [4] to provide the other methyl group at position 8. Also, in this step, benzylamine would replace methylamine, to lead to an N-benzyloxoisoquinuclidine, capable of manipulation to afford the azomethine group in mearsine.…”