Withanolide A: synthesis and structural requirements for neurite outgrowth

Liffert, Raphael and Hoecker, Johannes and Jana, Chandan K. and Woods, Tom M. and Burch, Patrick and Jessen, Henning J. and Neuburger, Markus and Gademann, Karl. (2013) Withanolide A: synthesis and structural requirements for neurite outgrowth. Chemical science, Vol. 4, H. 7. pp. 2851-2857.

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Official URL: http://edoc.unibas.ch/dok/A6223305

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann)
UniBasel Contributors:Gademann, Karl and Neuburger, Markus and Hoecker, Johannes David
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:31 Dec 2015 10:54
Deposited On:27 Feb 2014 15:45

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