Journal of the Chemical Society. Perkin transactions I p. 2306 - 2316 (1981)
Update date:2022-09-26
Topics:
Cairns, James
Logan, Robert T.
McGarry, George
Roy, Robert G.
Stevenson, Donald F. M.
Woods, Gilbert F.
The development of a 21-alkylation reaction which proceeds via the lithium 20(21)-enolate is described and ats scope demonstrated by the preparation of a variety of 21-alkylpregnane derivatives.Application of this process to 11β-acetoxy-16α,17α-dimethyl-5α-pregnane-3,20-dione (28a) and its 5β-analogue (28b) led to the corresponding 16α,17α,21-trimethyl derivatives.Several routes from these saturated trimethylpregnane-3,20-diones to 11β-hydroxy-16α,17α,21-trimethylpregna-1,4-diene-3,20-dione (Org 6216) were explored.The best method gave Org 6216 in 75percent yield.
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