Details
| Original language | English |
|---|---|
| Pages (from-to) | 1585-1588 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 22 |
| Issue number | 4 |
| Early online date | 30 Jan 2020 |
| Publication status | Published - 21 Feb 2020 |
| Externally published | Yes |
Abstract
The alleged structures of 5,6-epoxy-5,6-secosteroids fortisterol and herbarulide differ only in the stereoconfiguration of C24. Applying insights into the hypothetical biosynthesis of this class of natural products, we devised a short synthetic access (four and eight steps, respectively) starting from commercial ergosterol and featuring an alkoxy radical rearrangement. The comparison of nuclear magnetic resonance spectroscopic data revealed herbarulide having the proposed structure of fortisterol, whereas synthesis of another two diastereomers could not conclusively prove the true structure of fortisterol. Along the way, a high-yielding and scalable access to the infamous Burawoy's ketone not requiring chromium(VI) reagents was developed.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Organic letters, Vol. 22, No. 4, 21.02.2020, p. 1585-1588.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of the Alleged Structures of Fortisterol and Herbarulide and Structural Revision of Herbarulide
AU - Duecker, Fenja L.
AU - Heinze, Robert C.
AU - Mueller, Mira
AU - Zhang, Sudong
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by Deutsche Forschungsgemeinschaft (grant no. HE 7133/7-1) and the Boehringer Ingelheim Stiftung (exploration grant to P.H.). We acknowledge Dr. Carlo Fasting (FU Berlin) for HPLC separation and the assistance of the Core Facility BioSupraMol supported by the DFG.
PY - 2020/2/21
Y1 - 2020/2/21
N2 - The alleged structures of 5,6-epoxy-5,6-secosteroids fortisterol and herbarulide differ only in the stereoconfiguration of C24. Applying insights into the hypothetical biosynthesis of this class of natural products, we devised a short synthetic access (four and eight steps, respectively) starting from commercial ergosterol and featuring an alkoxy radical rearrangement. The comparison of nuclear magnetic resonance spectroscopic data revealed herbarulide having the proposed structure of fortisterol, whereas synthesis of another two diastereomers could not conclusively prove the true structure of fortisterol. Along the way, a high-yielding and scalable access to the infamous Burawoy's ketone not requiring chromium(VI) reagents was developed.
AB - The alleged structures of 5,6-epoxy-5,6-secosteroids fortisterol and herbarulide differ only in the stereoconfiguration of C24. Applying insights into the hypothetical biosynthesis of this class of natural products, we devised a short synthetic access (four and eight steps, respectively) starting from commercial ergosterol and featuring an alkoxy radical rearrangement. The comparison of nuclear magnetic resonance spectroscopic data revealed herbarulide having the proposed structure of fortisterol, whereas synthesis of another two diastereomers could not conclusively prove the true structure of fortisterol. Along the way, a high-yielding and scalable access to the infamous Burawoy's ketone not requiring chromium(VI) reagents was developed.
UR - http://www.scopus.com/inward/record.url?scp=85079049651&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.0c00180
DO - 10.1021/acs.orglett.0c00180
M3 - Article
VL - 22
SP - 1585
EP - 1588
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 4
ER -