Details
| Original language | English |
|---|---|
| Pages (from-to) | 8154-8157 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 27 |
| Issue number | 30 |
| Early online date | 22 Jul 2025 |
| Publication status | Published - 1 Aug 2025 |
Abstract
Tetracyclic natural products, which utilize the tetracycline skeleton, demonstrate a diverse array of biological activities. A critical structural feature of these compounds is the tertiary alcohol situated within a cis-decalin framework. In this study, we present a comprehensive protocol for the synthesis of tricyclic building blocks and complete carbon frameworks. This methodology facilitates the stereoselective synthesis of a specific enantiomer as well as its inversion to the corresponding opposite isomer via a ketol rearrangement.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic letters, Vol. 27, No. 30, 01.08.2025, p. 8154-8157.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - α-Ketol Rearrangement for Accessing Tetracyclic Natural Products
AU - Sara, Alexandru
AU - Eggert, Ulrike
AU - Kalesse, Markus
N1 - Publisher Copyright: © 2025 The Authors. Published by American Chemical Society
PY - 2025/8/1
Y1 - 2025/8/1
N2 - Tetracyclic natural products, which utilize the tetracycline skeleton, demonstrate a diverse array of biological activities. A critical structural feature of these compounds is the tertiary alcohol situated within a cis-decalin framework. In this study, we present a comprehensive protocol for the synthesis of tricyclic building blocks and complete carbon frameworks. This methodology facilitates the stereoselective synthesis of a specific enantiomer as well as its inversion to the corresponding opposite isomer via a ketol rearrangement.
AB - Tetracyclic natural products, which utilize the tetracycline skeleton, demonstrate a diverse array of biological activities. A critical structural feature of these compounds is the tertiary alcohol situated within a cis-decalin framework. In this study, we present a comprehensive protocol for the synthesis of tricyclic building blocks and complete carbon frameworks. This methodology facilitates the stereoselective synthesis of a specific enantiomer as well as its inversion to the corresponding opposite isomer via a ketol rearrangement.
UR - http://www.scopus.com/inward/record.url?scp=105012852507&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.5c02235
DO - 10.1021/acs.orglett.5c02235
M3 - Article
C2 - 40693678
AN - SCOPUS:105012852507
VL - 27
SP - 8154
EP - 8157
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 30
ER -