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

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 synthesis

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