Synthesis of digitoxigenin by remote functionalization |
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Authors: | Stephen F. Donovan Mitchell A. Avery John E. McMurry |
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Affiliation: | Thimann Laboratories, University of California, Santa Cruz, California 95064 U.S.A. |
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Abstract: | Treatment of a 21-hydroxy-20-keto steroid with the mixed anhydride of trifluoroacetic acid—diethylphosphonoacetic acid leads directly to cardenolides by an intramolecular Horner-Emmons reaction. Photolysis of 3β-acetoxy-5β,14α-card-20(22)-enolide and iodobenzenedichloride in benzene solution then yields 3β-acetoxy-5β-carda-14,20(22)-dienolide (β-anhydrodigitoxigenin acetate). |
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