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- W2326387718 endingPage "1059" @default.
- W2326387718 startingPage "1043" @default.
- W2326387718 abstract "Previously unknown 2α-hydroxy-5β-cholestane (Va) was synthesized from cholest-4-en-3-one (VI) in five steps and in the overall yield of 15·7% via the intermediate 2α-hydroxycholest-4-en-3-one (VIII). Oxidation of Va with Jones reagent afforded the 2-oxo-5β system which exhibits a negative Cotton effect curve symmetrical to that of the already known 2-oxo-5α system. Treatment of Va with lead tetraacetate in benzene afforded 2α,9α-epoxy-5β-cholestane (VII) as the result of a new transannular cyclization reaction from 2C to 9C in the 5β-steroid series. The 2α,9α-epoxide (VII) was converted to the 9α,11α-epoxide (XVII) via the 9(11)-eno intermediate (XVI). Reductive cleavage of XVII with lithium ethylamine afforded the 2α,9α-dihydroxy-5β system (XVIII). The stereochemistry of the reaction was confirmed by both physical and chemical data. The results obtained provide successful and stepwise functionalizations at 9C and 11C in the 5β-steroid steries with 2α-hydroxy compounds as starting material." @default.
- W2326387718 created "2016-06-24" @default.
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- W2326387718 date "1970-01-01" @default.
- W2326387718 modified "2023-10-18" @default.
- W2326387718 title "Studies on conformation and reactivity—VII" @default.
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- W2326387718 doi "https://doi.org/10.1016/s0040-4020(01)98781-2" @default.
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