Abstract
Reaction of 11-pregnene-3,20-dione ( 6 ) or 3-α-acetoxy-11-pregnen-20-one ( 12 ) with trimethylsilylethanesulfonyl (‘Ses’) iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11α,12α- N-methyl aziridinosteroids 9 and 15 , respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone ( 1 ).
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