Details
| Original language | English |
|---|---|
| Pages (from-to) | 21867-21871 |
| Number of pages | 5 |
| Journal | Journal of the American Chemical Society |
| Volume | 144 |
| Issue number | 48 |
| Early online date | 21 Nov 2022 |
| Publication status | Published - 7 Dec 2022 |
Abstract
The anthrasteroid rearrangement has been discussed for the formation of the eponymous substance class since its discovery. We here report its chemical emulation from a plausible biogenetic precursor and show how it accounts for the formation of asperfloketals A and B through a mechanistic bifurcation event. As a result, these natural products arise from double Wagner-Meerwein rearrangements and, thus, are 1(10→5),1(5→6)- and 1(10→5),4(5→6)diabeo-14,15-secosteroids, respectively. To establish an efficient route to a bioinspired precursor, we devised a sequence of orchestrated oxidative activation and rearrangement from ergosterol.
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Journal of the American Chemical Society, Vol. 144, No. 48, 07.12.2022, p. 21867-21871.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Chemical Emulation of the Biosynthetic Route to Anthrasteroids
T2 - Synthesis of Asperfloketal A
AU - Alekseychuk, Mykhaylo
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by the European Research Council (ERC Consolidator Grant “RadCrossSyn”), Deutsche Forschungsgemeinschaft (Heisenberg-Program HE 7133/8-1), and Boehringer Ingelheim Stiftung (plus3 perspectives program).
PY - 2022/12/7
Y1 - 2022/12/7
N2 - The anthrasteroid rearrangement has been discussed for the formation of the eponymous substance class since its discovery. We here report its chemical emulation from a plausible biogenetic precursor and show how it accounts for the formation of asperfloketals A and B through a mechanistic bifurcation event. As a result, these natural products arise from double Wagner-Meerwein rearrangements and, thus, are 1(10→5),1(5→6)- and 1(10→5),4(5→6)diabeo-14,15-secosteroids, respectively. To establish an efficient route to a bioinspired precursor, we devised a sequence of orchestrated oxidative activation and rearrangement from ergosterol.
AB - The anthrasteroid rearrangement has been discussed for the formation of the eponymous substance class since its discovery. We here report its chemical emulation from a plausible biogenetic precursor and show how it accounts for the formation of asperfloketals A and B through a mechanistic bifurcation event. As a result, these natural products arise from double Wagner-Meerwein rearrangements and, thus, are 1(10→5),1(5→6)- and 1(10→5),4(5→6)diabeo-14,15-secosteroids, respectively. To establish an efficient route to a bioinspired precursor, we devised a sequence of orchestrated oxidative activation and rearrangement from ergosterol.
UR - http://www.scopus.com/inward/record.url?scp=85142507040&partnerID=8YFLogxK
U2 - 10.1021/jacs.2c10735
DO - 10.1021/jacs.2c10735
M3 - Article
VL - 144
SP - 21867
EP - 21871
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 48
ER -