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Wittig rearrangement of 17(20)-ethylidene-16-furfuryloxy steroids 5–8 was examined. Reaction of 17E(20)-ethylidene-16α-furfuryloxy steroid 5 with t-BuLi in THF afforded (20S,22S)- and (20S,22R)-22-hydroxy steroids 9, 10 and 17Z(20)-ethylidene-16α-(2-furyl)hydroxymethyl steroid 11 in 61, 28, and 9% yields, respectively. Base treatment of 17E(20)-ethylidene-16β-furfuryloxy steroid 7 gave (20R,22R)-22-hydroxy...
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