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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
 
Creator VERMA, D
KUMAR, R
NAMBOOTHIRI, INN
 
Subject BESTMANN-OHIRA REAGENT
BASE-MEDIATED REACTION
PYRAZOLE ALKALOIDS
NEWBOULDIA-LAEVIS
REGIOSELECTIVE SYNTHESIS
RADICAL CYCLIZATION
SULFONYLPYRAZOLES
NITROALKENES
BARK
 
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.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-14T13:01:10Z
2014-10-14T13:01:10Z
2013
 
Type Article
 
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
 
Language en