Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 1322-1327 |
| Seitenumfang | 6 |
| Fachzeitschrift | Synthesis |
| Jahrgang | 55 |
| Ausgabenummer | 9 |
| Publikationsstatus | Veröffentlicht - 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.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
- Organische Chemie
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in: Synthesis, Jahrgang 55, Nr. 9, 23.02.2023, S. 1322-1327.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › 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 -