Construction of a γ-Butyrolactone Moiety: A Facile Synthesis of 3β- Hydroxy-5,6-Dihydro-17β -Methoxy-Pregnan-21,16α-Carbalactone - a New D-Ring Fused Steroidal γ-Butyrolactone from an Abundant 20- Oxopregnane using Metal Mediated Halogenation as the Key Step

Author(s): Preetismita Borah, Ashma Begum, Saroj Hazarika, Pritish Chowdhury.

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 8 , 2015

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Abstract:

A new D-ring fused steroidal γ-butyrolactone, 3β-hydroxy-5,6-dihydro-17β-methoxypregnan- 21,16α-carbalactone from abundant 20-oxopregnane,5,6-dihydro pregnenolone acetate using the high yield metal mediated C-21 functionalization reaction with MnO2-TMSCl/AcCl-AcOH system as the key step has been described. Furthermore, the application of this reaction paving a way to synthesize 3β,21-diacetoxy -16α,17α-epoxy-pregnan-20-one - a potent precursor towards the synthesis of a series of D-ring fused steroidal γ-butyrolactones has also been illustrated. The work highlights a convenient approach in constructing a D-ring fused steroidal γ-butyrolactone system from abundant 20-oxosteroids which might have general applicability in non-steroidal cyclic system.

Keywords: γ-Butyrolactones, D-ring fused Steroidal γ-Butyrolactones, Antitumor Steroids, 5α, 20- Oxopregnanes, C-21 Functionalization.

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Article Details

VOLUME: 12
ISSUE: 8
Year: 2015
Page: [566 - 573]
Pages: 8
DOI: 10.2174/157017861208150826115221
Price: $58

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