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
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 MnO 2 -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..
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Artikel |
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Erscheinungsjahr: |
2015 |
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Erschienen: |
2015 |
Enthalten in: |
Zur Gesamtaufnahme - volume:12 |
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Enthalten in: |
Letters in organic chemistry - 12(2015), 8, Seite 566-573 |
Sprache: |
Englisch |
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Beteiligte Personen: |
Preetismita Borah [VerfasserIn] |
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Links: |
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BKL: |
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doi: |
10.2174/157017861208150826115221 |
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funding: |
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Förderinstitution / Projekttitel: |
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PPN (Katalog-ID): |
OLC1961525259 |
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520 | |a 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 MnO 2 -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. | ||
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