Details
| Original language | English |
|---|---|
| Pages (from-to) | 1322-1327 |
| Number of pages | 6 |
| Journal | Synthesis |
| Volume | 55 |
| Issue number | 9 |
| Publication status | Published - 23 Feb 2023 |
Abstract
The biogenesis-inspired synthesis of the structurally unique 15(14 → 11)abeo-steroid penicillitone starting from commercially available ergosterol is reported. Key to the strategy is an intramolecular vinylogous aldol reaction of a 14,15-secoergostane obtained from the previously reported 14,15-secosteroid platform. Since a similar intermediate has been employed to access the strophasterol class of natural products, this work points at a possible biosynthetic connection between penicillitone and the strophasterols.
Keywords
- abeo -steroids, biogenesis-inspired synthesis, intramolecular vinylogous aldol reaction, penicillitone, strophasterol
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Synthesis, Vol. 55, No. 9, 23.02.2023, p. 1322-1327.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Biogenesis-Inspired Synthesis of Penicillitone
AU - Heretsch, Philipp
AU - Bauer, Maximilian
N1 - Funding Information: Financial support for this work was provided by the European Research Council (ERC Consolidator Grant 'RadCrossSyn', agreement no. 101043353), Deutsche Forschungsgemeinschaft (Heisenberg-Program HE 7133/8-1), and Boehringer Ingelheim Stiftung (plus3 perspectives program).
PY - 2023/2/23
Y1 - 2023/2/23
N2 - The biogenesis-inspired synthesis of the structurally unique 15(14 → 11)abeo-steroid penicillitone starting from commercially available ergosterol is reported. Key to the strategy is an intramolecular vinylogous aldol reaction of a 14,15-secoergostane obtained from the previously reported 14,15-secosteroid platform. Since a similar intermediate has been employed to access the strophasterol class of natural products, this work points at a possible biosynthetic connection between penicillitone and the strophasterols.
AB - The biogenesis-inspired synthesis of the structurally unique 15(14 → 11)abeo-steroid penicillitone starting from commercially available ergosterol is reported. Key to the strategy is an intramolecular vinylogous aldol reaction of a 14,15-secoergostane obtained from the previously reported 14,15-secosteroid platform. Since a similar intermediate has been employed to access the strophasterol class of natural products, this work points at a possible biosynthetic connection between penicillitone and the strophasterols.
KW - abeo -steroids
KW - biogenesis-inspired synthesis
KW - intramolecular vinylogous aldol reaction
KW - penicillitone
KW - strophasterol
UR - http://www.scopus.com/inward/record.url?scp=85153512878&partnerID=8YFLogxK
U2 - 10.1055/s-0042-1751422
DO - 10.1055/s-0042-1751422
M3 - Article
VL - 55
SP - 1322
EP - 1327
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 9
ER -