Unified Chemoenzymatic Approach to 16α-Methyl Glucocorticoids: Stereocontrolled Synthesis of (+)-Dexamethasone, (+)-Mometasone, (+)-Flumethasone, (+)-Halometasone, and (+)-Vamorolone.

Hangli He, Yajiao Zhang, Minjie Liu, Menglan Li, Zedu Huang, Fener Chen

Abstract read

In one paragraph

Article in JACS Au, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

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5 · Who and what money

Authors and funding

6 authors.

Hangli HeDepartment of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, State Key Laboratory of Green Chemical Synthesis and Conversion, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China.

Yajiao ZhangDepartment of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, State Key Laboratory of Green Chemical Synthesis and Conversion, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China.

Minjie LiuInstitute of Flow Chemistry and Engineering, College of Chemistry and Materials, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. China.

Menglan LiDepartment of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, State Key Laboratory of Green Chemical Synthesis and Conversion, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China.

Zedu HuangDepartment of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, State Key Laboratory of Green Chemical Synthesis and Conversion, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China.ORCID https://orcid.org/0000-0003-3320-3392

Fener ChenDepartment of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, State Key Laboratory of Green Chemical Synthesis and Conversion, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China.ORCID https://orcid.org/0000-0002-6734-3388

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

16α-Methyl glucocorticoids are a renowned family of steroid molecules with diverse important pharmaceutical applications, and development of innovative, practical, and divergent synthetic routes toward these steroids is highly desirable. Herein, we report a unified stereocontrolled synthesis of five 16α-methyl glucocorticoid pharmaceuticals, namely, (+)-dexamethasone, (+)-mometasone, (+)-flumethasone, (+)-halometasone, and (+)-vamorolone, in 9.9-26.8% overall yields starting from commercially available 9α-hydroxyandrost-4-ene-3,17-dione (9α-OH-AD), featuring a telescoped in-flow synthesis consisting of an acidic resin-mediated dehydration and an enzyme-catalyzed C1,2-dehydrogenation, an Au-(I)-catalyzed hydration of enyne to enone, and a conjugate addition-dihydroxylation sequence-enabled construction of the chiral C16α-methyl and C17α,21-dihydroxyacetone moieties. This established chemoenzymatic platform provides a versatile and generic access to other valuable 16α-methyl glucocorticoids.

Indexed as

16α-methyl glucocorticoidsasymmetric synthesisbiocatalysisconjugate addition-double hydroxylation sequenceflow chemistry

Identifiers

PMID42358698

DOI10.1021/jacsau.6c00382

PMCPMC13291877

What Socratic holds

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LicenceCC BY-NC-ND

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