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Synfacts 2020; 16(09): 1027
DOI: 10.1055/s-0040-1705869
Synthesis of Natural Products and Potential Drugs

Synthesis of Dexamethasone

Contributor(s):
Philip Kocienski
Ohta T, Zhang H, Torihara Y, Furukawa I. * Doshisha University, Kyoto, Japan
Improved Synthetic Route to Dexamethasone Acetate from Tigogenin.

Org. Process Res. Dev. 1997;
1: 420-424
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Key words

dexamethasone - corticosteroid - tigogenin - COVID-19 - conjugate addition

Significance

Dexamethasone is a corticosteroid that was first synthesized in 1957 and was approved in 1961 for the treatment of a wide range of inflammatory disorders. It is on the WHO List of Essential Medicines. In June 2020, dexamethasone was given preliminary approval for the treatment of COVID-19 because it improved survival rates of hospitalized patients receiving oxygen or on a ventilator. In 1997, Furukawa and co-workers reported a synthesis of dexamethasone from tigogenin.


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Comment

For the introduction of the 17α-hydroxy-16α-methyl moiety (B → E) the key epoxidation reaction was accomplished with peracetic acid in a buffer solution of sodium acetate and acetic acid (95% overall yield). Then the introduction of the 1,4-diene in the A-ring (H → J, 83% yield) was greatly improved by bromination–dehydrobromination, in which dehydrobromination proceeded smoothly in a mixture of DMF and 6% of water (83% yield).


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Publication History

Article published online:
18 August 2020

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