Steroids—CXX synthesis of halogenated steroid hormones
1959; Elsevier BV; Volume: 7; Issue: 1-2 Linguagem: Inglês
10.1016/0040-4020(59)80061-2
ISSN1464-5416
AutoresAlbert A. Bowers, Laura Cuéllar Ibáñez, Howard J. Ringold,
Tópico(s)Fluorine in Organic Chemistry
ResumoThe conformational and electronic factors involved in the fission of steroid 5α,6α-epoxides with boron trifluoride-etherate are discussed with particular reference to C-3-keto-5α,6α-epoxides and their cycloethylene-dioxy derivatives. These considerations led to the development of a new synthesis of 6-fluoro-Δ4-3-ketones from the corresponding Δ4-3-ketones via the boron trifluoride-etherate cleavage of their derived cycloethylene-ketal-5α,6α-epoxides. Application of this method led to the synthesis of 6α-fluorotestosterone and the 6α and 6β-fluoro analogs of progesterone desoxycorticosterone acetate and Reichstein's Compound “S” diacetate. The latter compound and its Δ1-analog are valuable precursors for the 6-fluoro cortical hormones.
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