Synthesis 2012; 44(24): 3822-3828
DOI: 10.1055/s-0032-1316816
paper
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approaches towards 4-Functionalized Estrone Derivatives

Uwe Schön
a   Abbott Products GmbH, Abbott Laboratories GmbH, Freundallee 9A, 30173 Hannover, Germany
,
Josef Messinger
a   Abbott Products GmbH, Abbott Laboratories GmbH, Freundallee 9A, 30173 Hannover, Germany
,
Wladimir Solodenko
b   Institut für Organische Chemie and Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany    Email: andreas.kirschning@oci.uni-hannover.de
,
Andreas Kirschning*
b   Institut für Organische Chemie and Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany    Email: andreas.kirschning@oci.uni-hannover.de
› Author Affiliations
Further Information

Publication History

Received: 05 August 2012

Accepted after revision: 28 September 2012

Publication Date:
05 November 2012 (online)


Abstract

Directed ortho-lithiation of estrone carbamate followed by reaction with electrophiles afforded 2-substituted estrone derivatives. Reductive cleavage of the carbamate group followed by O-allylation and Claisen rearrangement led to new 4-functionalized estrone derivatives.