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  Solvolysis of 14,17-etheno-bridged 16alpha-nitroestratrienyl acetate and lactam formation pathways studied by LC-NMR and LC-MS. Structures of minor products

Baranovsky, A., Bolibrukh, D. A., & Schneider, B. (2015). Solvolysis of 14,17-etheno-bridged 16alpha-nitroestratrienyl acetate and lactam formation pathways studied by LC-NMR and LC-MS. Structures of minor products. Steroids, 104, 37-48. doi:10.1016/j.steroids.2015.08.009.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0028-3559-0 Version Permalink: https://hdl.handle.net/21.11116/0000-0009-324B-B
Genre: Journal Article

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NMR224.pdf (Publisher version), 2MB
 
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NMR224s1.doc (Supplementary material), 5MB
 
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 Creators:
Baranovsky, Alexander, Author
Bolibrukh, Dmitry A., Author
Schneider, Bernd1, Author           
Affiliations:
1Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society, ou_421898              

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 Abstract: The ethanol solvolysis of 3-methoxy-14,17-etheno-16a-nitroestra-1,3,5(10)-trien-17b-yl acetate in the
presence of NaHCO3 was studied by means of real-time NMR experiments, LC–SPE–NMR, and LC–MS.
The pathway to form 3-methoxy-20-oxopyrrolidino-[40,50:14b,15b]-estra-1,3,5(10)-trien-17-one was
disclosed. The intermediacy of nitrile oxide and alkoxynitrone was postulated based on the analysis of
the reaction products. The proposed mechanism of cleaving the bridge in the nitro compound is legal
for the formation of N-acetoxylactams, nitriles, isoxazoles and isoxazolines.

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 Dates: 2015-08-152015-08-192015-12-19
 Publication Status: Issued
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 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: NMR224
DOI: 10.1016/j.steroids.2015.08.009
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Title: Steroids
Source Genre: Journal
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Publ. Info: Stoneham, MA [etc.] : Elsevier
Pages: - Volume / Issue: 104 Sequence Number: - Start / End Page: 37 - 48 Identifier: ISSN: 0039-128X
CoNE: https://pure.mpg.de/cone/journals/resource/954925446727