- Novel secosteroids arising from acid catalysed rearrangement of fluocinonide acetonide in the presence of Tf2O and TMSOTf
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Treatment of 6α,9α-difluoro-11β,21-dihydroxy-3,20-dioxo-16α, 17α- isopropylidenedioxypregna-1,4-diene-21-yl acetate (fluocinonide acetonide) with trifluoromethanesulfonic anhydride in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst gave the ketone 3 and furan 4 arising from cleavage of the C9-C10 bond and aromatisation of the A ring, and fluocinonide 5. The ketone 3 was shown to be an intermediate in the formation of furan 4.
- Procopiou, Panayiotis A.,Lynn, Sean M.,Roberts, Andrew D.
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- Preparation method of fluocinonide
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The invention relates to a preparation method of fluocinonide, in particular to preparation of fluocinonide. The preparation method of the fluocinonide comprises the following steps: taking chloride as an initiator; and successively carrying out 9,11-epoxy, 1,2-dehydrogenation, 17-dehydration, 6-fluorination, 9,11-ring-opening, 16,17-position double-bond dihydroxy oxidation, 21-position esterification and 16,17-position condensation to obtain the fluocinonide. The novel process has high industrial value, side effects can be controlled effectively, and reaction yield and quality are improved; high-risk reaction is not involved in technological design, and industrialization is easy to implement; and high-pollution reaction does not exist, and environmental protection treatment pressure is relieved.
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- Improved synthesis of fluocinolone acetonide and process research of 6α,9α-fluorination
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An efficient and improved synthetic route of fluocinolone acetonide with combination of bio-fermentation was developed from 21-acetyloxy-17α-hydroxy-4,9(11)-diene-3,20-dione (1a). Process of the 6α and 9α fluorination steps was studied, and it was observe
- Tang, Jie,Zeng, Chunling,Xie, Longyong,Wang, Jinghua,Tian, Mi,Guo, Cancheng
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supporting information
p. 110 - 112
(2018/01/26)
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