Details
| Original language | English |
|---|---|
| Pages (from-to) | 809-820 |
| Number of pages | 12 |
| Journal | SYNTHESIS-STUTTGART |
| Volume | 50 |
| Issue number | 4 |
| Publication status | Published - 18 Jan 2018 |
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.
Keywords
- abeo-steroids, benzilic acid rearrangement, i-steroids, natural products, total synthesis, abeo -steroids, i -steroids
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: SYNTHESIS-STUTTGART, Vol. 50, No. 4, 18.01.2018, p. 809-820.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Access to 5(6 -> 7)abeo-Steroids through Benzilic Acid Rearrangement of i-Steroids
AU - Noack, Florian
AU - Hartmayer, Bence
AU - Heretsch, Philipp
N1 - Funding information: This work was generously supported by Fonds der Chemischen Indus-trie (Sachkostenzuschuss to P.H.) and Freie Universität Berlin (For-schungskommissionsmittel to P.H.). )(
PY - 2018/1/18
Y1 - 2018/1/18
N2 - 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.
AB - 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.
KW - abeo-steroids
KW - benzilic acid rearrangement
KW - i-steroids
KW - natural products
KW - total synthesis
KW - abeo -steroids
KW - i -steroids
UR - http://www.scopus.com/inward/record.url?scp=85040797786&partnerID=8YFLogxK
U2 - 10.1055/s-0036-1591883
DO - 10.1055/s-0036-1591883
M3 - Article
VL - 50
SP - 809
EP - 820
JO - SYNTHESIS-STUTTGART
JF - SYNTHESIS-STUTTGART
SN - 0039-7881
IS - 4
ER -