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Synthesis 2018; 50(04): 809-820
DOI: 10.1055/s-0036-1591883
DOI: 10.1055/s-0036-1591883
paper
Access to 5(6→7)abeo-Steroids through Benzilic Acid Rearrangement of i-Steroids
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.
Key words
abeo-steroids - benzilic acid rearrangement - i-steroids - natural products - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591883.
- Supporting Information
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