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Issue 7, 2013
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Withanolide A: synthesis and structural requirements for neurite outgrowth

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Abstract

The exploration of different routes leading to the stereoselective synthesis of the neuritogenic steroid withanolide A is reported in full detail. Notable features of the synthesis include a Corey–Seebach homologation, a vinylogous aldol reaction, a singlet oxygen Schenck-ene reaction, and finally, a late-stage Wharton transposition. Semi-synthetic elaboration of the natural product resulted in 15 derivatives allowing a better understanding of its inherent reactivity pattern as well as its biological properties related to neuronal differentiation and neurite outgrowth.

Graphical abstract: Withanolide A: synthesis and structural requirements for neurite outgrowth

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Publication details

The article was received on 08 Mar 2013, accepted on 21 Apr 2013 and first published on 23 Apr 2013


Article type: Edge Article
DOI: 10.1039/C3SC50653C
Citation: Chem. Sci., 2013,4, 2851-2857
  • Open access: Creative Commons BY-NC license
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    Withanolide A: synthesis and structural requirements for neurite outgrowth

    R. Liffert, J. Hoecker, C. K. Jana, T. M. Woods, P. Burch, H. J. Jessen, M. Neuburger and K. Gademann, Chem. Sci., 2013, 4, 2851
    DOI: 10.1039/C3SC50653C

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