Details
| Original language | English |
|---|---|
| Pages (from-to) | 11574-11579 |
| Number of pages | 6 |
| Journal | Journal of the American Chemical Society |
| Volume | 144 |
| Issue number | 26 |
| Early online date | 21 Jun 2022 |
| Publication status | Published - 6 Jul 2022 |
Abstract
Triterpenoids and related abeo-steroids are of interest to the scientific community for their potent and varied biological activities as well as their unique structures. Within this large and diverse family of natural products, the fir metabolites (-)-spirochensilide A and B are particularly noteworthy for their controversial biogenesis. We herein report the chemical synthesis of the spirochensilides, which involves a concerted sequence of bioinspired rearrangements contributing to its resolution. Points of divergence after each rearrangement step also allow for an approach to the abifarine family of natural products with abifarine B as a synthetic target. Key to this strategy is a radical-polar crossover event to initiate the first rearrangement without the need for a sacrificial functionality to be introduced beforehand.
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In: Journal of the American Chemical Society, Vol. 144, No. 26, 06.07.2022, p. 11574-11579.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Biogenesis-Inspired, Divergent Synthesis of Spirochensilide A, Spirochensilide B, and Abifarine B Employing a Radical-Polar Crossover Rearrangement Strategy
AU - Alekseychuk, Mykhaylo
AU - Adrian, Sinan
AU - Heinze, Robert C.
AU - Heretsch, Philipp
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 - 2022/7/6
Y1 - 2022/7/6
N2 - Triterpenoids and related abeo-steroids are of interest to the scientific community for their potent and varied biological activities as well as their unique structures. Within this large and diverse family of natural products, the fir metabolites (-)-spirochensilide A and B are particularly noteworthy for their controversial biogenesis. We herein report the chemical synthesis of the spirochensilides, which involves a concerted sequence of bioinspired rearrangements contributing to its resolution. Points of divergence after each rearrangement step also allow for an approach to the abifarine family of natural products with abifarine B as a synthetic target. Key to this strategy is a radical-polar crossover event to initiate the first rearrangement without the need for a sacrificial functionality to be introduced beforehand.
AB - Triterpenoids and related abeo-steroids are of interest to the scientific community for their potent and varied biological activities as well as their unique structures. Within this large and diverse family of natural products, the fir metabolites (-)-spirochensilide A and B are particularly noteworthy for their controversial biogenesis. We herein report the chemical synthesis of the spirochensilides, which involves a concerted sequence of bioinspired rearrangements contributing to its resolution. Points of divergence after each rearrangement step also allow for an approach to the abifarine family of natural products with abifarine B as a synthetic target. Key to this strategy is a radical-polar crossover event to initiate the first rearrangement without the need for a sacrificial functionality to be introduced beforehand.
UR - http://www.scopus.com/inward/record.url?scp=85134360365&partnerID=8YFLogxK
U2 - 10.1021/jacs.2c05358
DO - 10.1021/jacs.2c05358
M3 - Article
VL - 144
SP - 11574
EP - 11579
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 26
ER -