Synthesis of Withasomnines and Their Non-natural Analogues from Aldehydes and 4-Nitro-1-butanol in Three Steps
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Title |
Synthesis of Withasomnines and Their Non-natural Analogues from Aldehydes and 4-Nitro-1-butanol in Three Steps
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Creator |
VERMA, D
KUMAR, R NAMBOOTHIRI, INN |
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Subject |
BESTMANN-OHIRA REAGENT
BASE-MEDIATED REACTION PYRAZOLE ALKALOIDS NEWBOULDIA-LAEVIS REGIOSELECTIVE SYNTHESIS RADICAL CYCLIZATION SULFONYLPYRAZOLES NITROALKENES BARK |
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Description |
Total synthesis of all three pyrazole-based withasomnine alkaloids and selected examples of their non-natural analogs has been achieved from readily available aldehydes and 4-nitro-1-butanol in three steps. Since 4-nitro-1-butanol in turn is prepared in two steps via Michael addition of nitromethane to acrylate followed by borane reduction of the ester group and the key 1,3-dipolar cycloaddition step is carried out with commercially available TMSCHN2, this approach is a very convenient and economical one.
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Publisher |
AMER CHEMICAL SOC
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Date |
2014-10-14T13:01:10Z
2014-10-14T13:01:10Z 2013 |
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Type |
Article
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Identifier |
JOURNAL OF ORGANIC CHEMISTRY, 78(7)3482-3486
http://dx.doi.org/10.1021/jo400207u http://dspace.library.iitb.ac.in/jspui/handle/100/14468 |
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Language |
en
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