Synthesis 2018; 50(04): 809-820
DOI: 10.1055/s-0036-1591883
paper
© Georg Thieme Verlag Stuttgart · New York

Access to 5(6→7)abeo-Steroids through Benzilic Acid Rearrangement of i-Steroids

Florian Noack
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany   Email: philipp.heretsch@fu-berlin.de
,
Bence Hartmayer
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany   Email: philipp.heretsch@fu-berlin.de
,
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany   Email: philipp.heretsch@fu-berlin.de
› Author Affiliations
This work was generously supported by Fonds der Chemischen Industrie (Sachkostenzuschuss to P.H.) and Freie Universität Berlin (Forschungskommissionsmittel to P.H.).
Further Information

Publication History

Received: 29 October 2017

Accepted after revision: 07 December 2017

Publication Date:
18 January 2018 (online)


Dedicated to Barbara, Kurt, and Konrad Krieger

Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry

Abstract

Benzilic acid rearrangement of i-steroid ketones and their subsequent opening gives access to 5(6→7)abeo-steroids. The functional group tolerance is demonstrated by several examples, including substrates with additional olefinic groups. The method opens a potential route to the synthesis of complex natural products such as solanioic acid from abundant steroid starting materials like ergosterol.

Supporting Information

 
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